Triazine ring-containing polymer, method for producing triazine ring-containing polymer, and non-photosensitive liquid composition

Abstract

The invention relates to a triazine ring-containing polymer, a method for producing the triazine ring-containing polymer, and a non-photosensitive liquid composition. The present invention addresses the problem of providing: a triazine ring-containing polymer capable of providing a molded article having a high refractive index and excellent light resistance or heat resistance; a method for producing the triazine ring-containing polymer; and a non-photosensitive liquid composition containing the triazine ring-containing polymer. [Solution] A liquid crystal composition containing a compound having a tert-butoxycarbonyloxy group, a triazine ring-containing polymer having a structural unit having a structure in which an aromatic group of a tert-butoxycarbonylamino group, a hydroxyl group protected by an acetal protecting group, or a carboxyl group protected by an acid-dissociable group is bonded to a triazine ring via a specific linking group, a polymer containing a triazine ring contains a structural unit that includes a structure in which an aromatic group is bonded to the triazine ring via a specific linking group and that is different from the structural unit, or a terminal group having a specific structure is bonded, or the weight-average molecular weight of the polymer containing the triazine ring is 4,000-20,000 (inclusive).

Description

Technical Field

[0001] The present invention relates to a polymer containing a structural unit having a specific structure, a method for producing the polymer, a non-photosensitive liquid composition containing the polymer, a method for producing a molded body using the non-photosensitive liquid composition, a molded body of the non-photosensitive liquid composition, an optical component formed from the molded body, and an optical element including the optical component. Background Art

[0002] Conventionally, in cameras, video cameras, etc., solid-state imaging devices have been used. In such solid-state imaging devices, CCD (charge-coupled device) image sensors and CMOS (complementary metal-oxide semiconductor) image sensors have been used. In the image sensors, fine condenser lenses (hereinafter referred to as microlenses) are provided for the purpose of increasing the light collection rate.

[0003] In recent years, CCD image sensors and CMOS image sensors have been further refined. Therefore, the diameter of the microlenses is being reduced. Even if the diameter of the microlens is small, in order to efficiently collect light in the photodiodes provided in the image sensor, it is necessary to increase the refractive index of the material of the microlens.

[0004] For example, as a high-refractive-index material that can be molded into various forms, a curable composition containing a photopolymerizable monomer (A) having a specific structure, metal oxide nanoparticles (B), and a photoinitiator (C) is known (see Patent Document 1).

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: Japanese Patent Application Laid-Open No. 2022-190405 Summary of the Invention

[0008] Problems to be Solved by the Invention

[0009] By using the curable composition described in Patent Document 1, a microlens having a high refractive index can be formed.

[0010] However, in order to cope with further reduction in the diameter of the microlens, a composition capable of forming a material having a higher refractive index is required. In addition, in high-refractive-index materials, excellent light resistance (the transparency does not decrease even when exposed to light for a long time) or excellent heat resistance (the transparency does not decrease even when exposed to high temperature for a long time) is also required.

[0011] The present invention has been made in view of such actual circumstances, and an object thereof is to provide a triazine ring-containing polymer capable of providing a molded article having a high refractive index and excellent light resistance or heat resistance, a method for producing the triazine ring-containing polymer, a non-photosensitive liquid composition containing the aforementioned triazine ring-containing polymer, a method for producing a molded article using the non-photosensitive liquid composition, a molded article of the non-photosensitive liquid composition, an optical component formed from the molded article, and an optical element including the optical component.

[0012] Means for Solving the Problem

[0013] The inventors of the present application have found that by including a structural unit in a triazine ring-containing polymer in which an aromatic group containing a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected with an acetal protecting group or a carboxyl group protected with an acid dissociable group is bonded to a triazine ring via a specific linking group, a structural unit containing a structure in which an aromatic group is bonded to a triazine ring via a specific linking group and different from the aforementioned structural unit, or a terminal group having a specific structure bonded thereto, or the weight average molecular weight of the aforementioned triazine ring-containing polymer is 4,000 or more and 20,000 or less, the above problems can be solved, and thus the present invention has been completed. Specifically, the present invention provides the following aspects.

[0014] A first aspect according to a first embodiment of the present invention is a triazine ring-containing polymer including a structural unit represented by the following formula (A1) and a structural unit represented by the following formula (A2).

[0015] [Chemical formula 1]

[0016]

[0017] (In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group,

[0018] R a1 is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group,

[0019] The hydroxyl group protected with an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 ,

[0020] R A1 is a hydrogen atom or an alkyl group,

[0021] R A2 is an alkyl group,

[0022] R A1 and R A2 can be bonded to each other to form a ring,

[0023] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0024] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0025] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 1 ;

[0026] X 2 is bonded to an aromatic ring in a group containing an aromatic group as Ar 2 .)

[0027] [Chemical Formula 2]

[0028]

[0029] (In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group,

[0030] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0031] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0032] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 3 ;

[0033] X 2 is bonded to an aromatic ring in a group containing an aromatic group as Ar 2 .)

[0034] The second mode according to the first embodiment of the present invention is a method for producing a polymer containing a triazine ring according to the first mode, which includes a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3),

[0035] The aforementioned dihalotriazine compound includes a compound represented by the following formula (A3) and a compound represented by the following formula (A6).

[0036] Ar 2 -(NR a2 H)2···(A5-1)

[0037] Ar 2 -(OH)2···(A5-2)

[0038] Ar 2 -(SH)2···(A5-3)

[0039] (In formulas (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.)

[0040] [Chemical formula 3]

[0041]

[0042] (In formula (A3), Hal is a halogen atom,

[0043] Ar 1 is a group containing an aromatic group,

[0044] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group,

[0045] The hydroxyl group protected with an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 wherein,

[0046] R A1 is a hydrogen atom or an alkyl group,

[0047] R A2 is an alkyl group,

[0048] R A1 and R A2 may be bonded to each other to form a ring,

[0049] X 1 each independently represents -NR a2 -, -O-, or -S-,

[0050] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0051] X 1 is bonded to Ar as 1The aromatic ring in the group containing an aromatic group.)

[0052] [Chemical Formula 4]

[0053]

[0054] (In formula (A6), Hal is a halogen atom,

[0055] Ar 3 is a group containing an aromatic group,

[0056] X 1 each independently is -NR a2 -, -O-, or -S-,

[0057] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0058] X 1 is bonded to the aromatic ring in the group containing an aromatic group as Ar 3 .)

[0059] The third aspect of the first embodiment of the present invention relates to a non-photosensitive liquid composition, which comprises a polymer (1A) containing a triazine ring and an organic solvent (S).

[0060] The polymer (1A) containing a triazine ring is the polymer containing a triazine ring according to the first aspect.

[0061] When R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further comprises a thermal acid generator (C).

[0062] The fourth aspect of the first embodiment of the present invention relates to a method for manufacturing a molded article, which includes the following steps:

[0063] A step of molding the non-photosensitive liquid composition according to the third aspect; and

[0064] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0065] The fifth aspect of the first embodiment of the present invention relates to a molded article of the non-photosensitive liquid composition according to the fourth aspect.

[0066] The sixth aspect of the first embodiment of the present invention relates to an optical component, which is formed from the molded article according to the fifth aspect.

[0067] The seventh mode according to the first embodiment of the present invention is an optical element, which includes the optical component according to the sixth mode.

[0068] The first mode according to the second embodiment of the present invention is a polymer containing a triazine ring, which includes a structural unit represented by the following formula (A1).

[0069] At least a part of the terminal of the molecular chain of the polymer containing a triazine ring has a group represented by the following formula (A1-1).

[0070] [Chemical formula 5]

[0071]

[0072] (In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group.

[0073] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected by an acetal protecting group, or a carboxyl group protected by an acid dissociable group.

[0074] The hydroxyl group protected by an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 .

[0075] R A1 is a hydrogen atom or an alkyl group.

[0076] R A2 is an alkyl group.

[0077] R A1 and R A2 may bond to each other to form a ring.

[0078] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-.

[0079] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0080] X 1 bonds to an aromatic ring in the group containing an aromatic group as Ar 1 .

[0081] X 2 bonds to an aromatic ring in the group containing an aromatic group as Ar 2 .)

[0082] -X2 -X 3 -X 4 ···(A1-1)

[0083] (In formula (A1-1), X 2 is the same as X in formula (A1). 2 Similarly,

[0084] X 3 is a divalent hydrocarbon group,

[0085] X 4 is -OR a3 or -N(R a3 )2,

[0086] R a3 is a hydrogen atom or an alkyl group which may have a substituent,

[0087] When the hydrocarbon group as X 3 is a group containing an aromatic group, X 4 is not an amino group.)

[0088] The second mode of the second embodiment of the present invention is a method for producing a polymer containing a triazine ring according to the first mode, which includes a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3),

[0089] The dihalotriazine compound includes a compound represented by the following formula (A3),

[0090] The condensation of the dihalotriazine compound with a compound represented by any one of the formulas (A5-1) to (A5-3) is carried out in the presence of a compound represented by any one of the following formulas (A7-1) to (A7-3), or

[0091] The condensation product of the dihalotriazine compound with a compound represented by any one of the formulas (A5-1) to (A5-3) is reacted with a compound represented by any one of the formulas (A7-1) to (A7-3).

[0092] Ar 2 -(NR a2 H)2···(A5-1)

[0093] Ar 2 -(OH)2···(A5-2)

[0094] Ar 2 -(SH)2···(A5-3)

[0095] (In formulas (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, Ra2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0096] [Chemical Formula 6]

[0097]

[0098] (In formula (A3), Hal is a halogen atom,

[0099] Ar 1 is a group containing an aromatic group,

[0100] R a1 is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected by an acetal protecting group, or is a carboxyl group protected by an acid-dissociable group,

[0101] The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -OR A2 The group represented by

[0102] R A1 is a hydrogen atom or an alkyl group,

[0103] R A2 is an alkyl group,

[0104] R A1 With R A2 can bond to each other to form a ring,

[0105] X 1 Each independently is -NR a2 -, -O- or -S-,

[0106] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0107] X 1 Bonded to Ar 1 The aromatic ring in the group containing an aromatic group.)

[0108] X 4 -X 3 -NR a2 H···(A7-1)

[0109] X 4 -X 3 -OH···(A7-2)

[0110] X 4 -X 3 -SH···(A7-3)

[0111] (In formulas (A7-1) to (A7-3), X 3 and X 4 are the same as X 3 and X 4 in formula (A1-1). Similarly,

[0112] R a2 is the same as R a2 in formula (A1).)

[0113] The third mode according to the second embodiment of the present invention is a non-photosensitive liquid composition, which contains a polymer (2A) containing a triazine ring and an organic solvent (S).

[0114] The polymer (2A) containing a triazine ring is the polymer containing a triazine ring according to the first mode.

[0115] When R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0116] The fourth mode according to the second embodiment of the present invention is a method for manufacturing a molded body, which includes the following steps:

[0117] A step of molding the non-photosensitive liquid composition according to the third mode; and

[0118] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0119] The fifth mode according to the second embodiment of the present invention is a molded body of the non-photosensitive liquid composition according to the fourth mode.

[0120] The sixth mode according to the second embodiment of the present invention is an optical component, which is formed from the molded body according to the fifth mode.

[0121] The seventh mode according to the second embodiment of the present invention is an optical element, which includes the optical component according to the sixth mode.

[0122] The first mode according to the third embodiment of the present invention is a polymer containing a triazine ring, which contains a structural unit represented by the following formula (A1), and the weight average molecular weight of the polymer containing a triazine ring is 4,000 or more and 20,000 or less.

[0123] [Chemical formula 7]

[0124]

[0125] (In formula (A1), Ar 1and Ar 2 is a group containing an aromatic group,

[0126] R a1 is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected by an acetal protecting group, or is a carboxyl group protected by an acid-dissociable group,

[0127] The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -OR A2 The group represented by

[0128] R A1 is a hydrogen atom or an alkyl group,

[0129] R A2 is an alkyl group,

[0130] R A1 With R A2 can bond to each other to form a ring,

[0131] X 1 and X 2 Each independently is -NR a2 -, -O- or -S-,

[0132] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0133] X 1 Bonded to Ar 1 The aromatic ring in the group containing an aromatic group,

[0134] X 2 Bonded to Ar 2 The aromatic ring in the group containing an aromatic group.)

[0135] The second aspect according to the third embodiment of the present invention is a method for producing a triazine ring-containing polymer according to the first aspect, comprising the step of condensing a dihalogenated triazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3).

[0136] The dihalogenated triazine compound includes a compound represented by the following formula (A3).

[0137] Ar 2 -(NR a2 H)2···(A5-1)

[0138] Ar 2 -(OH)2···(A5-2)

[0139] Ar2 -(SH)2···(A5-3)

[0140] (In formula (A5-1) to formula (A5-3), Ar 2 is a group containing an aromatic group, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0141] [Chemical Formula 8]

[0142]

[0143] (In formula (A3), Hal is a halogen atom,

[0144] Ar 1 is a group containing an aromatic group,

[0145] R a1 is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected by an acetal protecting group, or is a carboxyl group protected by an acid-dissociable group,

[0146] The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -OR A2 The group represented by

[0147] R A1 is a hydrogen atom or an alkyl group,

[0148] R A2 is an alkyl group,

[0149] R A1 With R A2 can bond to each other to form a ring,

[0150] X 1 Each independently is -NR a2 -, -O- or -S-,

[0151] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0152] X 1 Bonded to Ar 1 The aromatic ring in the group containing an aromatic group.)

[0153] The third aspect according to the third embodiment of the present invention is a non-photosensitive liquid composition comprising a triazine ring-containing polymer (3A) and an organic solvent (S).

[0154] The triazine ring-containing polymer (3A) is the triazine ring-containing polymer according to the first embodiment,

[0155] In R a1 When the hydroxyl group is protected with an acetal protecting group or the carboxyl group is protected with an acid dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0156] The fourth aspect according to the third embodiment of the present invention is a method for manufacturing a molded body, which includes the following steps:

[0157] A step of molding the non-photosensitive liquid composition according to the third aspect; and

[0158] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0159] The fifth aspect according to the third embodiment of the present invention is a molded body of the non-photosensitive liquid composition according to the fourth aspect.

[0160] The sixth aspect according to the third embodiment of the present invention is an optical component formed from the molded body according to the fifth aspect.

[0161] The seventh aspect according to the third embodiment of the present invention is an optical element having the optical component according to the sixth aspect.

[0162] Advantages of the Invention

[0163] According to the present invention, it is possible to provide a polymer capable of supplying a molded body having a high refractive index and excellent light resistance or heat resistance, a method for manufacturing the polymer, a non-photosensitive liquid composition containing the aforementioned polymer, a method for manufacturing a molded body using the non-photosensitive liquid composition, a molded body of the non-photosensitive liquid composition, an optical component formed from the molded body, and an optical element having the optical component. Detailed Embodiments

[0164] Hereinafter, the aforementioned first embodiment, second embodiment, and third embodiment will be described in sequence.

[0165] <<First Embodiment>>

[0166] <Polymer (1A) Containing a Triazine Ring>

[0167] The polymer (1A) containing a triazine ring contains a structural unit represented by the following formula (A1) and a structural unit represented by the following formula (A2). Hereinafter, the polymer (1A) containing a triazine ring is also referred to as "polymer (1A)".

[0168] The polymer of the structural unit represented by formula (A1) and the structural unit represented by formula (A2) exhibits a high refractive index, and even when exposed to light for a long time, the light transmittance is not easily reduced.

[0169] Hereinafter, the structural unit represented by formula (A1) will also be referred to as "unit (A1)". Other structural units other than the structural unit represented by formula (A1) will also be referred to as "unit (A2)".

[0170] [Chemical formula 9]

[0171]

[0172] In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group. R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group. The acetal protecting group is -CHR A1 -O-R A2 represents a group. R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may be bonded to each other to form a ring. X 1 and X 2 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 1 . X 2 is bonded to an aromatic ring in the group containing an aromatic group as Ar 2 .

[0173] [Chemical formula 10]

[0174]

[0175] In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group. X 1 and X 2 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 3The aromatic ring in the group containing an aromatic group. X 2 is bonded to an aromatic ring in the group as Ar 2 in the group containing an aromatic group.

[0176] The polymer (1A) containing unit (A1) and unit (A2) has a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group.

[0177] The above polymer (1A) is soluble in various organic solvents such as nitrogen-containing polar organic solvents and ketone solvents.

[0178] However, by deprotecting the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or by deprotecting the carboxyl group protected with an acid dissociable group, the above polymer (1A) becomes poorly soluble in organic solvents. The deprotected polymer (1A) having a hydroxyl group, an amino group, or a carboxyl group can be crosslinked with a polymerizable monomer capable of reacting with the hydroxyl group, the amino group, or the carboxyl group, and thus becomes even more poorly soluble in organic solvents. As the polymerizable monomer, a crosslinkable compound (B) described later can be mentioned.

[0179] Therefore, the above polymer (1A) is easily processed as a solution. On the other hand, a molded article produced using a solution of the aforementioned polymer under conditions for deprotecting the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or the carboxyl group protected with an acid dissociable group is poorly soluble in organic solvents.

[0180] The ratio of the total mass of unit (A1) and unit (A2) to the mass of the polymer (1A) is not particularly limited as long as the desired effects are not impaired. Regarding the ratio of the total mass of unit (A1) and unit (A2) to the mass of the polymer (1A), it is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 80% by mass or more, particularly preferably 90% by mass or more, and most preferably 100% by mass, based on the mass of the polymer (1A).

[0181] The ratio of the number of moles of unit (A1) to the total number of moles of unit (A1) and unit (A2) is preferably 10 mol% or more and 70 mol% or less, more preferably 20 mol% or more and 70 mol% or less, and particularly preferably 30 mol% or more and 60 mol% or less.

[0182] [Unit (A1)]

[0183] In formula (A1), Ar 1 and Ar2 is a group containing an aromatic group. The group containing an aromatic group may be a group composed only of aromatic groups, or may have non-aromatic groups together with aromatic groups.

[0184] The group containing an aromatic group may contain only 1 aromatic group, or may contain 2 or more aromatic groups. The aromatic group contained in the group containing an aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group. The aromatic group contained in the group containing an aromatic group is preferably an aromatic hydrocarbon group.

[0185] The aromatic group contained in the group containing an aromatic group may be a monocyclic group or a polycyclic group. The polycyclic group may be a fused-ring group, or may be a group formed by connecting 1 or more rings selected from monocyclic groups and polycyclic groups by single bonds. The fused-ring group may be a group formed by fusing aromatic groups, or may be a group formed by fusing an aromatic group and an aliphatic cyclic group.

[0186] The number of aromatic monocycles contained in the group containing an aromatic group is not particularly limited as long as the desired effect is not impaired. It should be noted that when the group containing an aromatic group is an aromatic fused-ring group, the number of monocycles constituting the aromatic fused-ring is regarded as the number of aromatic monocycles contained in the group containing an aromatic group. Specifically, when the group containing an aromatic group is a naphthalenediyl group, the number of aromatic monocycles contained in the group containing an aromatic group is 2.

[0187] The number of aromatic monocycles contained in the group containing an aromatic group is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and further preferably 1 or 2.

[0188] As preferred examples of the group containing an aromatic group, groups represented by the following formulas (a-1) to (a-11) can be cited.

[0189] [Chemical formula 11]

[0190]

[0191] In formulas (a-1) to (a-11), R a01 are each independently a group selected from the group consisting of a halogen atom, a sulfonic acid group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0192] R a02 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.

[0193] W a1 and W a2 each independently represents a single bond, -CR a03 R a04 -represents a group, a carbonyl group, -O-, -S-, -SO-, -SO2-, or -NR a05 -represents a group.

[0194] R a03 and R a04 are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. -CR a03 R a04 -in the represented group, R a03 and R a04 can be bonded to each other to form a ring.

[0195] R a05 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

[0196] X a1 and X a2 each independently represents a single bond, an alkylene group having 1 to 10 carbon atoms, or -Y a1 -Ph-Y a2 -represents a group.

[0197] Ph is a phenylene group which may have 1 to 4 substituents. The substituents that the phenylene group may have are groups selected from the group consisting of a halogen atom, a sulfonic acid group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0198] Y a1 and Y a2 each independently represents a single bond or an alkylene group having 1 to 10 carbon atoms.

[0199] n1 is an integer of 0 to 4.

[0200] n2 and n3 each independently are integers of 0 to 3.

[0201] n4 is an integer of 0 to 2.

[0202] n5 is an integer of 0 to 3.

[0203] n6 and n7 each independently are integers of 0 to 3.

[0204] n8 is an integer of 0 to 3.

[0205] n9 is an integer of 0 to 5.

[0206] n10 and n11 each independently are integers of 0 to 3.

[0207] n12 is an integer of 0 or more and 3 or less.

[0208] n13 is an integer of 0 or more and 4 or less.

[0209] n14, n15 and n16 are each independently an integer of 0 or more and 4 or less.

[0210] n17 is an integer of 0 or more and 3 or less.

[0211] n18 is an integer of 0 or more and 4 or less.

[0212] n19 is an integer of 0 or more and 5 or less.

[0213] n20 and n21 are integers of 0 or more and 4 or less.

[0214] n22 and n23 are integers of 0 or more and 4 or less.

[0215] Regarding the halogen atom as R a01 Examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Among them, a fluorine atom, a chlorine atom and a bromine atom are preferred.

[0216] As the alkyl group having 1 to 10 carbon atoms as R a01 it may be linear or branched. Regarding the specific examples of the alkyl group having 1 to 10 carbon atoms as R a01 examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a tert-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a 2-ethylhexyl group, a n-nonyl group and a n-decyl group.

[0217] As the alkoxy group having 1 to 10 carbon atoms as R a01 it may be linear or branched. Regarding the specific examples of the alkoxy group having 1 to 10 carbon atoms as R a01 examples thereof include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentyloxy group, an isopentyloxy group, a tert-pentyloxy group, a n-hexyloxy group, a n-heptyloxy group, a n-octyloxy group, a 2-ethylhexyloxy group, a n-nonyloxy group and a n-decyloxy group.

[0218] As the alkyl group having 1 to 10 carbon atoms as R a02 is the same as the alkyl group having 1 to 10 carbon atoms as R a01 Regarding the R

[0219] Regarding the R a02Specific examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms include phenyl, naphthalen-1-yl, naphthalen-2-yl, 4-phenylphenyl, 3-phenylphenyl, and 2-phenylphenyl.

[0220] Specific examples of the aralkyl group having 7 to 13 carbon atoms include benzyl, phenethyl, 3-phenyl-n-propyl, naphthalen-1-ylmethyl, and naphthalen-2-ylmethyl.

[0221] W a1 and W a2 each independently represents a single bond, a group represented by -CR a03 R a04 -, a carbonyl group, -O-, -S-, -SO-, -SO2-, or a group represented by -NR a05 -.

[0222] In the case where W a1 and W a2 are groups represented by -CR a03 R a04 -, R a03 and R a04 are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

[0223] The alkyl group having 1 to 10 carbon atoms as R a03 and R a04 is the same as the alkyl group having 1 to 10 carbon atoms as R a01 .

[0224] R a03 and R a04 may be bonded to each other to form a ring.

[0225] In the case where W a1 and W a2 are groups represented by -NR a05 -, R a05 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

[0226] The alkyl group having 1 to 10 carbon atoms as R a05 is the same as the alkyl group having 1 to 10 carbon atoms as R a01 .

[0227] X a1 and X a2 each independently represents a single bond, an alkylene group having 1 to 10 carbon atoms, or a group represented by -Y a1 -Ph-Y a2 -.

[0228] Regarding X a1 and X a2Specific examples of the alkylene group having 1 to 10 carbon atoms include methylene, ethane-1,2-diyl (ethylene), ethane-1,1-diyl, propane-1,3-diyl, propane-1,2-diyl, propane-1,1-diyl, propane-2,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl and decane-1,10-diyl.

[0229] In X a1 and X a2 -Y a1 -Ph-Y a2 In the case of a group represented by -, Ph is a phenylene group which may have 1 to 4 substituents. The substituents which the phenylene group may have are selected from the group consisting of a halogen atom, a sulfonic acid group, an alkyl group having 1 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms.

[0230] The alkyl group having 1 to 10 carbon atoms and the alkoxy group having 1 to 10 carbon atoms as the substituent that the phenylene group may have and the a01 The same applies to an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms.

[0231] Y a1 and Y a2 Each independently represents a single bond or an alkylene group having 1 to 10 carbon atoms.

[0232] As Y a1 and Y a2 The alkylene group having 1 to 10 carbon atoms and X a1 and X a2 The same applies to an alkylene group having 1 to 10 carbon atoms.

[0233] Specific examples of the groups represented by formula (a-1) to formula (a-11) include the following groups.

[0234] [Chemical Formula 12]

[0235]

[0236] [Chemical Formula 13]

[0237]

[0238] Among the above-mentioned groups, the following groups are preferred.

[0239] [Chemical Formula 14]

[0240]

[0241] In formula (A1), R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group.

[0242] Tert-butoxycarbonyloxy and tert-butoxycarbonylamino can be deprotected only by heating. On the other hand, a hydroxyl group protected with an acetal protecting group and a carboxyl group protected with an acid dissociable group are difficult to deprotect only by heating. In order to deprotect a hydroxyl group protected with an acetal protecting group and a carboxyl group protected with an acid dissociable group by heating, for example, it is advantageous to heat the protected hydroxyl group or the protected carboxyl group in the co-presence of the thermal acid generator (C) described later. In this case, the hydroxyl group protected with an acetal protecting group and the carboxyl group protected with an acid dissociable group can be easily deprotected by the action of the acid generated by heating the thermal acid generator (C).

[0243] As described above, from the viewpoint of being easily deprotected only by heating, as R a1 , tert-butoxycarbonyloxy and tert-butoxycarbonylamino are preferred, and tert-butoxycarbonylamino is more preferred. [[ID=1,4]]

[0244] The acetal protecting group is a group represented by -CHR A1 -O-R A2 is a group represented by.

[0245] R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may be bonded to each other to form a ring.

[0246] As R A1 and R A2 , the alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. As R A1 and R A2 , the alkyl group may be linear or branched, and is preferably linear.

[0247] Regarding preferred specific examples of the alkyl group as R A1 and R A2 , methyl, ethyl, n-propyl, and n-butyl can be mentioned.

[0248] As -CHR A1 -O-R A2Specific examples of the group represented include methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1-n-propoxyethyl, 1-n-butoxyethyl, tetrahydropyran-2-yl, and tetrahydrofuran-2-yl.

[0249] As the acid dissociable group, there is no particular limitation as long as it is a group known in the technical fields of organic synthesis, photoresists, etc. and can protect a carboxyl group. Preferred examples of the acid dissociable group include acetal protecting groups and groups containing a tertiary carbon atom.

[0250] As the acetal protecting group, it is preferably the group represented by the aforementioned -CHR A1 -O-R A2 .

[0251] As the group containing a tertiary carbon atom, it is preferably the group represented by -C(R A3 )(R A4 )(R A5 ).

[0252] R A3 、R A4 and R A5 are each independently an alkyl group having 1 to 6 carbon atoms, a fluoroalkyl group having a 1 to 6 carbon atoms, or an aliphatic cyclic group having 5 to 20 carbon atoms.

[0253] Regarding specific examples of the alkyl group as R A3 、R A4 and R A5 , there can be mentioned methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

[0254] As the fluoroalkyl group of R A3 、R A4 and R A5 is a group obtained by substituting part or all of the hydrogen atoms of the above alkyl group with fluorine atoms.

[0255] Regarding specific examples of the aliphatic cyclic group as R A3 、R A4 and R A5 , there can be mentioned groups obtained by removing one or more hydrogen atoms from polycyclic alkanes such as monocyclic alkanes, bicyclic alkanes, tricyclic alkanes, and tetracyclic alkanes. Specifically, there can be mentioned groups obtained by removing one hydrogen atom from monocyclic alkanes such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, and polycyclic alkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane. Particularly preferred are groups obtained by removing one hydrogen atom from cyclohexane and adamantane (which may further have substituents).

[0256] As the group represented by -C(R A3 )(R A4 )(R A5 ), the following groups can be cited as specific examples.

[0257] [Chemical formula 15]

[0258]

[0259] In formula (A1), X 1 and X 2 are each independently -NR a2 -, -O- or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0260] The number of carbon atoms of the alkyl group as R a2 is not particularly limited. The number of carbon atoms of the alkyl group as R a2 is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less. The alkyl group as R a2 can be linear or branched, and is preferably linear.

[0261] Regarding specific examples of the alkyl group as R a2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and n-hexyl can be cited.

[0262] Regarding the substituents that the alkyl group as R a2 may have, halogen atoms, hydroxyl groups, alkoxy groups, mercapto groups and cyano groups can be cited.

[0263] The number of carbon atoms of the aromatic hydrocarbon group as R a2 is not particularly limited. The number of carbon atoms of the alkyl group as R a2 is preferably 6 or more and 12 or less.

[0264] Regarding specific examples of the aromatic hydrocarbon group as R a2 , phenyl, naphthalen-1-yl, naphthalen-2-yl, 4-phenylphenyl, 3-phenylphenyl and 2-phenylphenyl can be cited.

[0265] Regarding the substituents that the aromatic hydrocarbon group as R a2 may have, halogen atoms, alkyl groups, hydroxyl groups, alkoxy groups, mercapto groups and cyano groups can be cited.

[0266] The X 1 in formula (A1) is bonded to the aromatic ring in the group containing an aromatic group as Ar 1 . The X 2 in formula (A1) is bonded to the group as Ar2 The aromatic ring in the group containing an aromatic group.

[0267] X described above 2 is preferably -NR a2 - or -O-, more preferably -NR a2 -. In the case where X 2 is -NR a2 -, in the structural unit represented by formula (A1), the twist of the triazine ring and Ar 2 is small. As a result, the planarity of the structural unit represented by formula (A1) is high. It is considered that if the planarity of the structural unit represented by formula (A1) is high, the refractive index of the polymer (1A) having the structural unit represented by formula (A1) is high.

[0268] As a preferred specific example of unit (A1), the following structural units can be cited. In addition, the structural units obtained by changing the amino group bonded to the triazine ring in the following structural units to -O- or -S- are also preferred. In addition, the structural units obtained by changing the tert-butoxycarbonylamino group in the following structural units to tert-butoxycarbonyloxy are also preferred. In addition, the structural units obtained by changing the tert-butoxycarbonyl group in the following structural units to methoxymethyl, ethoxymethyl, n-propyloxymethyl, n-butyloxymethyl, 1-methoxyethyl, 1-ethoxymethyl, 1-n-propyloxyethyl, 1-n-butyloxyethyl, tetrahydropyran-2-yl, or tetrahydrofuran-2-yl are also preferred.

[0269] [Chemical formula 16]

[0270]

[0271] [Chemical formula 17]

[0272]

[0273] [Chemical formula 18]

[0274]

[0275] [Chemical formula 19]

[0276]

[0277] [Unit (A2)]

[0278] As described above, the polymer (1A) contains unit (A2) as another structural unit other than unit (A1).

[0279] Unit (A2) is a structural unit represented by the following formula (A2).

[0280] [Chemical formula 20]

[0281]

[0282] In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group. X 1 and X 2 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group which is Ar 3 . X 2 is bonded to an aromatic ring in the group containing an aromatic group which is Ar 2 .

[0283] Unit (A2) does not belong to unit (A1). Therefore, the group containing an aromatic group which is Ar 3 may not have a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, a hydroxyl group protected with an acetal protecting group, and a carboxyl group protected with an acid dissociable group as substituents.

[0284] In formula (A2), X 1 , X 2 and Ar 2 are the same as X 1 , X 2 and Ar 2 in formula (A1). In formula (A2), Ar 3 is an aromatic group which may have a substituent. The aromatic group which is Ar 3 may be an aromatic hydrocarbon group or an aromatic heterocyclic group. Regarding the aromatic group which is Ar 3 , an aromatic hydrocarbon group is preferred.

[0285] Regarding specific examples of the aromatic hydrocarbon group which is Ar 3 , phenyl, naphthalen-1-yl, naphthalen-2-yl, 4-phenylphenyl, 3-phenylphenyl, and 2-phenylphenyl can be mentioned.

[0286] Regarding the substituents which the aromatic hydrocarbon group which is Ar 3 may have, a halogen atom, an alkyl group, an alkoxy group, and a cyano group can be mentioned.

[0287] The above-mentioned polymer (1A) can be obtained by reacting a dihalotriazine compound represented by the following formula (A3) and a dihalotriazine compound represented by the following formula (A6) with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0288] In this case, the polymer (1A) is mostly a mixture of molecules having halogen atoms at both ends, molecules having a halogen atom at one end and an amino group, a hydroxyl group, or a mercapto group at the other end, and molecules having an amino group, a hydroxyl group, or a mercapto group at both ends.

[0289] When the polymer (1A) has a halogen terminal derived from a dihalotriazine compound represented by the following formula (A3) or a dihalotriazine compound represented by the following formula (A6), it is also preferable to cap the halogen terminal with an amine compound having one amino group. Such a polymer (1A) having a terminal capped with an amine compound can be obtained by reacting the halogen atom at the terminal in the polymer with the above-mentioned amine compound.

[0290] That is, the polymer (1A) obtained by capping the terminal with an amine compound has an N-substituted amino group or an N,N-disubstituted amino group obtained by removing one hydrogen atom bonded to the nitrogen atom from the amine compound used for capping as a terminal group.

[0291] When the polymer (1A) contains molecules having halogen terminals, since the molecules having halogen atoms at the terminals react with the molecules having an amino group, a hydroxyl group, or a mercapto group at the terminals, during the storage of the non-photosensitive liquid composition, the molecular weight of the polymer (1A) increases, and the properties of the non-photosensitive liquid composition change over time.

[0292] However, if the halogen terminals in the polymer (1A) are capped with an amine compound, the change in the properties of the non-photosensitive liquid composition over time can be suppressed.

[0293] When capping the halogen terminals in the polymer (1A) with an amine compound, it is also preferable to prepare a polymer (1A) having halogen terminals at both ends and then cap the two halogen terminals of the obtained polymer (1A) with an amine compound.

[0294] The polymer having halogen terminals at both ends can be produced by the following method: When producing the polymer (1A) by the following method, a dihalotriazine compound represented by the following formula (A3) and a dihalotriazine compound represented by the following formula (A6) are used for an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0295] In addition, when the polymer (1A) has an amino group, a hydroxyl group, or a mercapto group derived from an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3) at the terminal, the polymer (1A) having an amino group, a hydroxyl group, or a mercapto group at the terminal can be reacted with a dihalotriazine compound represented by the formula (A3) and a dihalotriazine compound represented by the formula (A6), whereby both terminals of the polymer (1A) are converted into halogen terminals derived from the dihalotriazine compound represented by the formula (A3) or the dihalotriazine compound represented by the formula (A6).

[0296] The amine compound used for end-capping can be a primary amine or a secondary amine, and a primary amine is preferred.

[0297] As the amine compound for the terminal chain, a hydrocarbon compound substituted with an amino group is preferred, and alkylamine, cycloalkylamine, aralkylamine, and arylamine are preferred.

[0298] The number of carbon atoms of the alkylamine is preferably 1 or more and 10 or less, more preferably 2 or more and 8 or less, and further preferably 2 or more and 6 or less.

[0299] Specific examples of the alkylamine include ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, n-pentylamine, n-hexylamine, n-heptylamine, n-octylamine, 2-ethylhexylamine, n-nonylamine, and n-decylamine.

[0300] The number of carbon atoms of the cycloalkylamine is preferably 3 or more and 10 or less, more preferably 3 or more and 8 or less, and further preferably 3 or more and 6 or less.

[0301] Specific examples of the cycloalkylamine include cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, cycloheptylamine, cyclooctylamine, cyclononylamine, and cyclodecylamine.

[0302] The number of carbon atoms of the aralkylamine is preferably 7 or more and 20 or less, more preferably 7 or more and 12 or less.

[0303] Specific examples of the aralkylamine include benzylamine, phenethylamine, naphthalen-1-ylmethylamine, and naphthalen-2-ylmethylamine.

[0304] The number of carbon atoms of the arylamine is preferably 6 or more and 20 or less, more preferably 6 or more and 12 or less.

[0305] Specific examples of the arylamine include aniline, 1-aminonaphthalene, 2-aminonaphthalene, 4-phenylaniline, 3-phenylaniline, and 2-phenylaniline.

[0306] The weight-average molecular weight of the polymer (1A) is not particularly limited as long as the desired effects are not impaired. The weight-average molecular weight is preferably 500 or more and 100,000 or less. From the viewpoint of the high solvent resistance of the polymer in a heated state, the weight-average molecular weight is preferably 2,000 or more. From the viewpoint of the high solubility of the polymer (1A) in various solvents, the weight-average molecular weight is preferably 30,000 or less.

[0307] The weight-average molecular weight is the molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0308] <Method for producing polymer (1A)>

[0309] The method for producing the polymer (1A) described above is not particularly limited as long as the resulting polymer (1A) contains the unit (A1) and the unit (A2).

[0310] Typically, the above polymer (1A) is produced by condensing a dihalotriazine compound with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0311] The dihalotriazine compound used for producing the polymer (1A) includes the compound represented by the following formula (A3) and the compound represented by the following formula (A6).

[0312] [Chemical formula 21]

[0313]

[0314] In formula (A3), Hal is a halogen atom. Ar 1 is a group containing an aromatic group. R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group. The acetal protecting group is -CHR A1 -O-R A2 represents a group. R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may bond to each other to form a ring. X 1 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 bonds to an aromatic ring in the group containing an aromatic group as Ar 1 ​

[0315] In formula (A3), Ar 1 , X 1 and R a1 are the same as Ar 1 , X 1 and R a1 in formula (A1). Hal is a halogen atom. Examples of Hal include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, a chlorine atom and a bromine atom are preferred, and a chlorine atom is more preferred.

[0316] [Chemical formula 22]

[0317]

[0318] In formula (A6), Hal is a halogen atom. Ar 3 is a group containing an aromatic group. X 1 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 3 .

[0319] In formula (A6), Ar 3 and X 1 are the same as Ar 3 and X 1 in formula (A2).

[0320] Ar 2 -(NR a2 H)2···(A5-1)

[0321] Ar 2 -(OH)2···(A5-2)

[0322] Ar 2 -(SH)2···A5-3)

[0323] In formulas (A5-1) to (A5-3), Ar 2 and R a2 are the same as Ar 2 and R a2 in formula (A1).

[0324] As specific examples of the aromatic diamine compound represented by the formula (A5-1), p-phenylenediamine, m-phenylenediamine, 2,4-diaminotoluene, 4,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 3,4'-diaminobiphenyl, 1,4-diaminonaphthalene, 1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 2,7-diaminonaphthalene, 9,10-diaminoanthracene, 9,10-bis(4-aminophenyl)anthracene, 4,4'-diamino-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, 3,4'-diaminobenzophenone, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 3,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfide, 3,3'-diaminodiphenylsulfide, 3,4'-diaminodiphenylsulfide, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)propane, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 4,4'-diaminobenzanilide, 3,3'-diaminobenzanilide, 1,4-bis(4-aminophenyl)benzene, 1,3-bis(4-aminophenyl)benzene, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 1,2-bis(4-aminophenoxy)ethane, 1,3-bis(4-aminophenoxy)propane, 1,4-bis(4-aminophenoxy)butane, 1,5-bis(4-aminophenoxy)pentane, 1,6-bis(4-aminophenoxy)hexane, bis[4-(4-aminophenoxy)phenyl]ether, bis[4-(3-aminophenoxy)phenyl]ether, 4,4'-bis(4-aminophenoxy)biphenyl, 3,4'-bis(4-aminophenoxy)biphenyl, 3,3'-bis(4-aminophenoxy)biphenyl, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]ketone, 2,2-bis[4-{4-amino-2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-aminophenyl)fluorene, 9,9-bis(4-amino-3-methylphenyl)fluorene, 2,7-diaminofluorene, 2-(4-aminophenyl)-5-aminobenzoxazole, 2-(3-aminophenyl)-5-aminobenzoxazole, 2-(4-aminophenyl)-6-aminobenzoxazole, 2-(3-aminophenyl)-6-aminobenzoxazole, 1,4-bis(5-amino-2-benzoxazolyl)benzene, 1,4-bis(6-amino-2-benzoxazolyl)benzene, 1,3-bis(5-amino-2-benzoxazolyl)benzene, 1,3-bis(6-amino-2-benzoxazolyl)benzene, 2,6-bis(4-aminophenyl)benzobisoxazole, 2,6-bis(3-aminophenyl)benzobisoxazole, bis[(3-aminophenyl)-5-benzoxazolyl], bis[(4-aminophenyl)-5-benzoxazolyl], bis[(3-aminophenyl)-6-benzoxazolyl], bis[(4-aminophenyl)-6-benzoxazolyl], 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 4,4'-[1,4-phenylenebis(1-methylethane-1,1-diyl)]dianiline, 4-aminophenyl 4-aminobenzoate, 1,3-bis(4-anilinyl)tetramethyldisiloxane, 1,4-bis(3-aminopropyldimethylsilyl)benzene, o-tolidine sulfone, etc.,

[0325] As specific examples of the aromatic diol represented by the formula (A5-2), hydroquinone, resorcinol, 2,4-dihydroxytoluene, 4,4'-dihydroxybiphenyl, 3,3'-dihydroxybiphenyl, 3,4'-dihydroxybiphenyl, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 9,10-dihydroxyanthracene, 9,10-bis(4-hydroxyphenyl)anthracene, 4,4'-dihydroxy-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-dihydroxybenzophenone, 3,3'-dihydroxybenzophenone, 3,4'-dihydroxybenzophenone, 4,4'-dihydroxydiphenyl sulfone, 3,3'-dihydroxydiphenyl sulfone, 3,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfide, 3,3'-dihydroxydiphenyl sulfide, 3,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenylmethane, 3,3'-diaminodiphenylmethane, 3,4'-dihydroxydiphenylmethane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis[4-(4-hydroxyphenoxy)phenyl]propane, 2,2-bis[4-(4-hydroxyphenoxy)phenyl]hexafluoropropane, 4,4'-dihydroxydiphenyl ether, 3,4'-dihydroxydiphenyl ether, 3,3'-dihydroxydiphenyl ether, 4,4'-dihydroxybenz anilide, 3,3'-dihydroxybenz anilide, 1,4-bis(4-hydroxyphenyl)benzene, 1,3-bis(4-hydroxyphenyl)benzene, 1,4-bis(4-hydroxyphenoxy)benzene, 1,3-bis(4-hydroxyphenoxy)benzene, 1,3-bis(3-hydroxyphenoxy)benzene, 1,2-bis(4-hydroxyphenoxy)ethane, 1,??-bis(4-hydroxyphenoxy)propane, 1,4-bis(4-hydroxyphenoxy)butane, 1,5-bis(4-hydroxyphenoxy)pentane, 1,6-bis(4-hydroxyphenoxy)hexane, bis[4-(4-hydroxyphenoxy)phenyl]ether, bis[4-(3-hydroxyphenoxy)phenyl]ether, 4,4'-bis(4-hydroxyphenoxy)biphenyl, 3,4'-bis(4-hydroxyphenoxy)biphenyl, 3,3'-bis(4-hydroxyphenoxy)biphenyl, bis(4-hydroxyphenoxyphenyl)sulfone, bis(3-hydroxyphenoxyphenyl)sulfone, bis[4-(4-hydroxyphenoxy)phenyl]sulfone, bis[4-(3-hydroxyphenoxy)phenyl]sulfone, bis[4-(4-hydroxyphenoxy)phenyl]ketone, 2,2-bis[4-{4-hydroxy-2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 2,7-dihydroxyfluorene, 2-(4-hydroxyphenyl)-5-hydroxybenzoxazole, 2-(3-hydroxyphenyl)-5-hydroxybenzoxazole, 2-(4-hydroxyphenyl)-6-hydroxybenzoxazole, 2-(3-hydroxyphenyl)-6-hydroxybenzoxazole, 1,4-bis(5-hydroxy-2-benzoxazolyl)benzene, 1,4-bis(6-hydroxy-2-benzoxazolyl)benzene, 1,3-bis(5-hydroxy-2-benzoxazolyl)benzene, 1,3-bis(6-hydroxy-2-benzoxazolyl)benzene, 2,6-bis(4-hydroxyphenyl)benzobisoxazole, 2,6-bis(3-hydroxyphenyl)benzobisoxazole, bis[(3-hydroxyphenyl)-5-benzoxazolyl], bis[(4-hydroxyphenyl)-5-benzoxazolyl], bis[(3-hydroxyphenyl)-6-benzoxazolyl], bis[(4-hydroxyphenyl)-6-benzoxazolyl], 3,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfide, 4,4'-[1,4-phenylenebis(1-methylethane-1,1-diyl)]dianiline, 4-hydroxyphenyl 4-hydroxybenzoate, 1,3-bis(4-anilino)tetramethyldisiloxane, etc.,

[0326] As specific examples of the aromatic dithiol represented by the formula (A5-3), 1,4-benzenedithiol, 1,3-benzenedithiol, 2,4-dimercaptotoluene, 4,4'-biphenyldithiol, 3,3'-biphenyldithiol, 3,4'-biphenyldithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 2,7-naphthalenedithiol, 9,10-anthracenedithiol, 9,10-bis(4-mercaptophenyl)anthracene, 4,4'-dimercapto-2,2'-bis(trifluoromethyl)biphenyl, 4,4'-dithiobenzophenone, 3,3'-dithiobenzophenone, 3,4'-dithiobenzophenone, 4,4'-dithiodiphenyl sulfone, 3,3'-dithiodiphenyl sulfone, 3,4'-dithiodiphenyl sulfone, 4,4'-dithiodiphenyl sulfide, 3,3'-dithiodiphenyl sulfide, 3,4'-dithiodiphenyl sulfide, 4,4'-dithiobiphenylmethane, 3,3'-diaminodiphenylmethane, 3,4'-dithiobiphenylmethane, 2,2-bis(4-mercaptophenyl)propane (bisphenol A), 2,2-bis[4-(4-mercaptophenoxy)phenyl]propane, 2,2-bis[4-(4-mercaptophenoxy)phenyl]hexafluoropropane, 4,4'-dithiodiphenyl ether, 3,4'-dithiodiphenyl ether, 3,3'-dithiodiphenyl ether, 4,4'-dithiobenzanilide, 3,3'-dithiobenzanilide, 1,4-bis(4-mercaptophenyl)benzene, 1,3-bis(4-mercaptophenyl)benzene, 1,4-bis(4-mercaptophenoxy)benzene, 1,3-bis(4-mercaptophenoxy)benzene, 1,3-bis(3-mercaptophenoxy)benzene, 1,2-bis(4-mercaptophenoxy)ethane, 1,3-bis(4-mercaptophenoxy)propane, 1,4-bis(4-mercaptophenoxy)butane, 1,5-bis(4-mercaptophenoxy)pentane, 1,6-bis(4-mercaptophenoxy)hexane, bis[4-(4-mercaptophenoxy)phenyl] ether, bis[4-(3-mercaptophenoxy)phenyl] ether, 4,4'-bis(4-mercaptophenoxy)biphenyl, 3,4'-bis(4-mercaptophenoxy)biphenyl, 3,3'-bis(4-mercaptophenoxy)biphenyl, bis(4-mercaptophenoxyphenyl) sulfone, bis(3-mercaptophenoxyphenyl) sulfone, bis[4-(4-mercaptophenoxy)phenyl] sulfone, bis[4-(3-mercaptophenoxy)phenyl] sulfone, bis[4-(4-mercaptophenoxy)phenyl] ketone, 2,2-bis[4-{4-mercapto-2-(trifluoromethyl)phenoxy}phenyl]hexafluoropropane, 9,9-bis(4-mercaptophenyl)fluorene, 9,9-bis(4-mercapto-3-methylphenyl)fluorene, 2,7-dithiofluorene, 2-(4-mercaptophenyl)-5-mercaptobenzoxazole, 2-(3-mercaptophenyl)-5-mercaptobenzoxazole, 2-(4-mercaptophenyl)-6-mercaptobenzoxazole, 2-(3-mercaptophenyl)-6-mercaptobenzoxazole, 1,4-bis(5-mercapto-2-benzoxazolyl)benzene, 1,4-bis(6-mercapto-2-benzoxazolyl)benzene, 1,3-bis(5-mercapto-2-benzoxazolyl)benzene, 1,3-bis(6-mercapto-2-benzoxazolyl)benzene, 2,6-bis(4-mercaptophenyl)benzobisoxazole, 2,6-bis(3-mercaptophenyl)benzobisoxazole, bis[(3-mercaptophenyl)-5-benzoxazolyl], bis[(4-mercaptophenyl)-5-benzoxazolyl], bis[(3-mercaptophenyl)-6-benzoxazolyl], bis[(4-mercaptophenyl)-6-benzoxazolyl], 3,4'-dimercapto diphenyl sulfide, 4,4'-dimercapto diphenyl sulfide, 4,4'-[1,4-phenylene bis(1-methylethane-1,1-diyl)]dianiline, 4-mercaptobenzoic acid 4-mercaptophenyl ester, 1,3-bis(4-anilino)tetramethyldisiloxane, etc.,

[0327] The dihalotriazine compound represented by the formula (A3) can be produced by condensing cyanuric halide with an aromatic amine compound represented by the following formula (A3-1), a hydroxyaromatic compound represented by the following formula (A3-2), or a mercaptoaromatic compound represented by the following formula (A3-3).

[0328] R a1 -Ar 1 -NR a2 H···(A3-1)

[0329] R a1 -Ar 1 -OH···(A3-2)

[0330] R a1 -Ar 1 -SH···(A3-3)

[0331] In the formulas (A3-1) to (A3-3), Ar 1 , R a1 and R a2 are the same as Ar 1 , R a1 and R a2 in the formula (A1).

[0332] Examples of the cyanuric halide include cyanuric fluoride, cyanuric chloride, and cyanuric bromide. Among them, cyanuric chloride is preferred.

[0333] Regarding the usage amount of the aromatic amine compound represented by the formula (A3-1), the hydroxyaromatic compound represented by the formula (A3-2), or the mercaptoaromatic compound represented by the formula (A3-3) in the production of the dihalotriazine compound represented by the formula (A3), relative to 1 mole of cyanuric halide, it is preferably 0.8 mole or more and 1.2 moles or less, more preferably 0.9 mole or more and 1.1 moles or less, and still more preferably 0.95 mole or more and 1.05 moles or less.

[0334] The reaction of cyanuric halide with the aromatic amine compound represented by formula (A3-1), the hydroxyaromatic compound represented by formula (A3-2), or the mercaptoaromatic compound represented by formula (A3-3) is usually carried out by mixing the two in an organic solvent.

[0335] The organic solvent used in the above reaction is not particularly limited as long as the reaction proceeds well. Considering from the aspect of not reacting with cyanuric halide, solvents without hydroxyl group, mercapto group or amino group are preferred. Specific examples of the organic solvent include, for example, ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, p-xylene, o-xylene, m-xylene, ethylbenzene and styrene; monoalkyl ether acetates of glycols such as ethylene glycol methyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate and diethylene glycol monoethyl ether acetate; dialkyl ethers of glycols such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether and triethylene glycol dimethyl ether; esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate and isobutyl acetate; lactones such as γ-butyrolactone.

[0336] The amount of the organic solvent used is not particularly limited as long as the reaction proceeds well. Relative to 100 parts by mass of the reaction raw materials, the amount of the organic solvent used is preferably 100 parts by mass or more and 5000 parts by mass or less, more preferably 200 parts by mass or more and 4000 parts by mass or less.

[0337] The temperature for reacting cyanuric halide with the aromatic amine compound represented by formula (A3-1), the hydroxyaromatic compound represented by formula (A3-2), or the mercaptoaromatic compound represented by formula (A3-3) is, for example, preferably -20°C or higher and 150°C or lower, more preferably -10°C or higher and 50°C or lower.

[0338] When the aromatic amine compound represented by formula (A3-1), the hydroxyaromatic compound represented by formula (A3-2), or the mercaptoaromatic compound represented by formula (A3-3) has tert-butoxycarbonyloxy or tert-butoxycarbonylamino as R a1 in the case, in order to prevent the deprotection of tert-butoxycarbonyloxy or tert-butoxycarbonylamino caused by heat, the reaction temperature is preferably -10°C or higher and 50°C or lower.

[0339] The reaction time is not particularly limited. For example, the reaction time is preferably 30 minutes or more and 50 hours or less, more preferably 1 hour or more and 30 hours or less.

[0340] As preferred specific examples of the aromatic amine compound represented by formula (A3-1), the hydroxyaromatic compound represented by formula (A3-2), and the mercaptoaromatic compound represented by formula (A3-3), the following compounds can be cited. R in the following formula a1 is the same as R in formula (A1). a1 Similarly.

[0341] [Chemical formula 23]

[0342]

[0343] [Chemical formula 24]

[0344]

[0345] [Chemical formula 25]

[0346]

[0347] By using the dihalotriazine compound represented by formula (A6) together with the dihalotriazine compound represented by formula (A3), units (A1) and (A2) can be obtained.

[0348] The method for condensing the dihalotriazine compound containing the dihalotriazine compound represented by formula (A3) and the dihalotriazine compound represented by formula (A6) with the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol represented by formula (A5-3) is not particularly limited.

[0349] Typically, the dihalotriazine compound containing the dihalotriazine compound represented by formula (A3) and the dihalotriazine compound represented by formula (A6) can be mixed with the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol in an organic solvent to produce the aforementioned polymer (1A).

[0350] The organic solvent used in the condensation reaction is preferably an organic solvent in which the resulting polymer (1A) is soluble. Examples of such organic solvents include nitrogen-containing polar organic solvents such as N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylformamide, N-methylformamide, N,N-dimethylpropionamide, N,N-dimethylisobutyramide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methyl-2-piperidone, N-acetylpyrrolidine, N,N'-dimethylethyleneurea (1,3-dimethyl-2-imidazolidinone), N,N'-dimethylpropyleneurea, N,N,N',N'-tetramethylpropanediamide, N-methylcaprolactam, N,N,N',N'-tetramethylurea, 3-methoxy-N,N-dimethylpropionamide, and 3-butoxy-N,N-dimethylpropionamide; sulfoxides such as dimethyl sulfoxide; hexamethylphosphoric triamide; ketone solvents such as cyclopentanone, cyclohexanone, and methyl isobutyl ketone; and ethers such as tetrahydrofuran and dioxane.

[0351] The amount of the organic solvent used is not particularly limited as long as the reaction proceeds well. Relative to 100 parts by mass of the reaction raw materials, the amount of the organic solvent used is preferably 100 parts by mass or more and 5000 parts by mass or less, more preferably 200 parts by mass or more and 4000 parts by mass or less.

[0352] Regarding the amount of the aromatic diamine compound represented by the formula (A5-1), the aromatic diol represented by the formula (A5-2), or the aromatic dithiol represented by the formula (A5-3) used in the production of the polymer (1A), relative to 1 mole of the dihalotriazine compound containing the dihalotriazine compound represented by the formula (A3) and the dihalotriazine compound represented by the formula (A6), it is preferably 0.8 mole or more and 1.2 moles or less, more preferably 0.9 mole or more and 1.1 moles or less, and further preferably 0.95 mole or more and 1.05 moles or less.

[0353] When producing the polymer (1A), the terminals of the polymer (1A) may or may not be end-capped, but end-capping is preferred.

[0354] The reaction temperature in the production of the polymer (1A) by polymerization is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower.

[0355] The reaction temperature for end-capping the terminals of the polymer (1A) is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower, and further preferably 20°C or higher and 60°C or lower.

[0356] The reaction temperature in the production of the polymer (1A) by polymerization is preferably higher than the reaction temperature for end-capping the terminals of the polymer.

[0357] The reaction time is not particularly limited. For example, when producing the polymer (1A) by polymerization, the reaction time is preferably 5 minutes or more and 48 hours or less, more preferably 10 minutes or more and 40 hours or less, and still more preferably 30 minutes or more and 30 hours or less.

[0358] When end-capping the polymer (1A), the reaction time is preferably 5 minutes or more and 12 hours or less, more preferably 10 minutes or more and 6 hours or less, and still more preferably 30 minutes or more and 3 hours or less.

[0359] When producing the polymer (1A) by polymerization, the reaction time is preferably longer than the reaction time for end-capping the polymer (1A).

[0360] <Non-photosensitive liquid composition>

[0361] The non-photosensitive liquid composition contains the aforementioned polymer (1A) and an organic solvent (S).

[0362] When the aforementioned polymer (A) has a hydroxyl group protected with an acetal protecting group as R a1 or R a1 is a carboxyl group protected with an acid-dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0363] After shaping the above non-photosensitive liquid composition into a desired shape by methods such as coating or casting, the non-photosensitive liquid composition is heated to remove the organic solvent (S), whereby a shaped body can be obtained.

[0364] At this time, tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group is deprotected by heating to generate a hydroxyl group or an amino group. Therefore, the polymer component contained in the shaped body is not easily soluble in the organic solvent.

[0365] In addition, when the polymer (1A) has a hydroxyl group protected with an acetal protecting group or a carboxyl group protected with an acid-dissociable group as R a1 the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0366] When the above non-photosensitive liquid composition is heated, the hydroxyl group protected with an acetal protecting group or the carboxyl group protected with an acid-dissociable group is deprotected by the action of the acid generated by the thermal acid generator (C) to generate a hydroxyl group or a carboxyl group. Therefore, the polymer component contained in the shaped body is not easily soluble in the organic solvent.

[0367] In addition, the non-photosensitive liquid composition preferably contains a crosslinkable compound (B). When the polymer (A) is heated, a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected with an acetal protecting group is deprotected, or a carboxyl group protected with an acid dissociable group is deprotected, thereby generating a hydroxyl group, an amino group, or a carboxyl group. Since the deprotected polymer (1A) is crosslinked with the crosslinkable compound (B) capable of reacting with a hydroxyl group, an amino group, or a carboxyl group, the non-photosensitive liquid composition is cured to form a cured product that is hardly soluble in an organic solvent.

[0368] [Polymer (1A)]

[0369] The polymer (1A) is the aforementioned polymer (1A) containing a structural unit represented by formula (A1).

[0370] [Crosslinkable compound (B)]

[0371] The crosslinkable compound (B) is not particularly limited as long as it is a compound having two or more crosslinkable groups capable of reacting with a hydroxyl group, an amino group, or a carboxyl group.

[0372] From the aspect of the height of the refractive index of the cured product formed by heating the non-photosensitive liquid composition, preferably, the crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups, a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups.

[0373] The sulfur-containing compound (Bii) is a compound that does not belong to the aromatic compound (Bi).

[0374] The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii).

[0375] The crosslinkable group is a group capable of reacting with a phenolic hydroxyl group, an amino group, or a carboxyl group to effect crosslinking. Preferred examples of the crosslinkable group include an epoxy group, a thiirane group, and an isocyanate group.

[0376] The above crosslinkable compound (B) crosslinks the polymer (1A') derived from the aforementioned polymer (1A) and having a phenolic hydroxyl group, an amino group, or a carboxyl group generated by deprotection, whereby a cured product having a high refractive index can be formed using the non-photosensitive liquid composition.

[0377] In particular, when the above crosslinkable compound (B) is an isocyanate compound (Biii), since a carbonyl group is present at the crosslinking site, the refractive index does not decrease, and thus it is preferred from this point of view.

[0378] Hereinafter, a compound containing two or more crosslinkable groups and a triazine ring is also referred to as "crosslinkable triazine compound (Bi-1)". A compound containing two or more crosslinkable groups and a fluorene ring is also referred to as "crosslinkable fluorene compound (Bi-2)". A compound containing two or more crosslinkable groups and a binaphthalene ring is also referred to as "crosslinkable binaphthalene compound (Bi-3)".

[0379] (Crosslinkable triazine compound (Bi-1))

[0380] As the crosslinkable triazine compound (Bi-1), a compound represented by the following formula (b1) is preferred.

[0381] [Chemical formula 26]

[0382]

[0383] In formula (b1), Ar b1 , Ar b2 and Ar b3 are each independently a group containing an aromatic group. R b1 , R b2 and R b3 are a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, a cyano group, -O-CO-NH-X b4 a group represented by -NCO, a glycidyloxy group or a thiirane-2-ylmethyloxy group. X b1 , X b2 and X b3 are each independently -NR b4 -, -O- or -S-. X b4 is a divalent organic group. Two or three of R b1 , R b2 and R b3 are glycidyloxy groups or thiirane-2-ylmethyloxy groups. R b4 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X b1 is bonded to an aromatic ring in the group containing an aromatic group as Ar b1 . X b2 is bonded to an aromatic ring in the group containing an aromatic group as Ar b2 . X b3 is bonded to an aromatic ring in the group containing an aromatic group as Ar b3 .

[0384] In formula (b1), as Ar b1 , Ar b2 and Ar b3The group containing an aromatic group is the same as Ar in the aforementioned formula (A1). 1 Preferably, Ar b1 , Ar b2 and Ar b3 are the same group containing an aromatic group.

[0385] R in formula (b1) b4 is the same as R in the aforementioned formula (A1). a2

[0386] As R b1 , R b2 and R b3 The number of carbon atoms of the alkyl group is not particularly limited. As R b1 , R b2 and R b3 The number of carbon atoms of the alkyl group is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less.

[0387] Regarding specific examples of the alkyl group as R b1 , R b2 and R b3 , examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and n-hexyl.

[0388] As R b1 , R b2 and R b3 The number of carbon atoms of the alkoxy group is not particularly limited. As R b1 , R b2 and R b3 The number of carbon atoms of the alkoxy group is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less.

[0389] Regarding specific examples of the alkoxy group as R b1 , R b2 and R b3 , examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy and n-hexyloxy.

[0390] When R b1 , R b2 or R b3 is a group represented by -O-CO-NH-X b4 -NCO, the group represented by -O-CO-NH-X b4 -NCO can be formed by bonding to Ar b1 , Ar b2 and Ar b3 ​The hydroxyl group on the group containing an aromatic group reacts with an excess amount of a diisocyanate compound and is introduced into the compound represented by the formula (b1).

[0391] X b4 is a divalent organic group. X b4 is a divalent organic group, typically a residue obtained by removing two isocyanate groups from a diisocyanate compound.

[0392] As an example of the diisocyanate compound that can be used to introduce the group represented by -O-CO-NH-X b4 -NCO, there can be mentioned chain aliphatic diisocyanates such as 1,4-butane diisocyanate, 1,6-hexane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and dimer acid diisocyanate; alicyclic diisocyanates such as 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate), bis(4-isocyanatocyclohexyl)methane, and norbornane diisocyanate; aromatic diisocyanates such as 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, 1,4-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, 1,5-naphthalene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, and α,α,α',α'-tetramethylphenylene diisocyanate.

[0393] As R b1 、R b2 and R b3 , preferably, -X b4 -CO-NH-X b5 -NCO represents a group, a glycidyloxy group, and a thiirane-2-ylmethyloxy group, which are crosslinkable groups, and more preferably a glycidyloxy group and a thiirane-2-ylmethyloxy group.

[0394] As a preferred example of the compound represented by the formula (b1), the following compounds can be mentioned.

[0395] [Chemical formula 27]

[0396]

[0397] [Chemical formula 28]

[0398]

[0399] [Chemical Formula 29]

[0400]

[0401] [Chemical Formula 30]

[0402]

[0403] (Crosslinkable Fluorene Compound (Bi-2))

[0404] As the crosslinkable fluorene compound (Bi-2), in terms of easy synthesis and acquisition, good crosslinking reactivity, and easy obtainment of a cured product with a high refractive index, the compound represented by the following formula (b2) is preferred.

[0405] [Chemical Formula 31]

[0406]

[0407] (In formula (b2), W 1 and W 2 are each independently a group represented by the following formula (b2-1),

[0408] [Chemical Formula 32]

[0409]

[0410] In formula (b2-1), ring Z represents an aromatic hydrocarbon ring, X represents a single bond or a group represented by -S-, R 1 represents a single bond, an alkylene group having 1 to 4 carbon atoms, or an alkyleneoxy group having 1 to 4 carbon atoms. When R 1 is an alkyleneoxy group, the oxygen atom in the alkyleneoxy group is bonded to ring Z, and R 2 represents a monovalent hydrocarbon group, a hydroxyl group, a group represented by -OR 4a , a group represented by -SR 4b , an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by -NHR 4c , a group represented by -N(R 4d )2, a sulfo group, or at least a part of the hydrogen atoms bonded to the carbon atoms contained in a monovalent hydrocarbon group, a group represented by -OR 4a , a group represented by -SR 4b , an acyl group, an alkoxycarbonyl group, a group represented by -NHR 4c or a group represented by -N(R 4d )2 is substituted with a monovalent hydrocarbon group, a hydroxyl group, a group represented by -OR 4a , a group represented by -SR 4bThe groups, acyl groups, alkoxycarbonyl groups, halogen atoms, nitro groups, cyano groups, mercapto groups, carboxyl groups, amino groups, carbamoyl groups, -NHR 4c The groups, -N(R 4d )2, the groups obtained by substitution with methanesulfonyloxy or sulfo group, R 4a ~R 4d independently represent monovalent hydrocarbon groups, m represents an integer of 0 or more, R 3 is -CO-NH-X b4 the group represented by -NCO, thiirane-2-ylmethyl or glycidyl,

[0411] ring Y 1 and ring Y 2 represent the same or different aromatic hydrocarbon rings, R 3a and R 3b independently represent a cyano group, a halogen atom or a monovalent hydrocarbon group, t1 and t2 independently represent an integer of 0 or more and 4 or less.)

[0412] In the above formula (b2-1), as ring Z, for example, a benzene ring, a condensed polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, a naphthalene ring, etc., a C 8-20 fused bicyclic hydrocarbon ring, preferably a C 10-16 fused bicyclic hydrocarbon ring), a fused tricyclic aromatic hydrocarbon ring (for example, an anthracene ring, a phenanthrene ring, etc.) and other fused 2- to 4-ring aromatic hydrocarbon rings] etc. Ring Z is preferably a benzene ring or a naphthalene ring, more preferably a naphthalene ring. It should be noted that W 1 and W 2 are each independently a group represented by formula (b2-1), therefore, W 1 and W 2 each contain ring Z. The ring Z contained in W 1 and the ring Z contained in W 2 can be the same or different. For example, one ring can be a benzene ring and the other ring can be a naphthalene ring, etc., but it is particularly preferred that any one ring is a naphthalene ring.

[0413] In addition, the substitution position of ring Z bonded via X on the carbon atom directly connecting W 1 and W 2 is not particularly limited. For example, when ring Z is a naphthalene ring, the group corresponding to ring Z bonded to the above carbon atom can be 1-naphthyl, 2-naphthyl, etc.

[0414] In formula (b2-1), X independently represents a single bond or a group represented by -S-, typically a single bond.

[0415] In formula (b2-1), as R 1, for example, single bonds; alkylene groups having 1 to 4 carbon atoms, such as methylene, ethylene, trimethylene, propylene, butane-1,2-diyl, etc.; alkyleneoxy groups having 1 to 4 carbon atoms, such as methyleneoxy, ethyleneoxy, propyleneoxy, etc., preferably single bonds; C 2-4 Alkylene (especially ethylene, propylene, etc. C 2-3 Alkylene); C 2-4 Alkyleneoxy (especially ethyleneoxy, propyleneoxy, etc. C 2-3 Alkylene), more preferably a single bond. 1 When it is an alkyleneoxy group, the oxygen atom in the alkyleneoxy group is bonded to the ring Z. In addition, since W in formula (b2) 1 and W 2 Each independently represents a group represented by formula (b2-1), so W 1 and W 2 Each contains R as a divalent group 1 .W 1 R included in 1 With W 2 R included in 1 It can be the same or different.

[0416] In formula (b2-1), R 2 For example, alkyl groups (e.g., methyl, ethyl, propyl, isopropyl, butyl, etc.) 1-12 Alkyl, preferably C 1-8 Alkyl, more preferably C 1-6 Alkyl, etc.), cycloalkyl (cyclohexyl, etc. C 5-10 Cycloalkyl, preferably C 5-8 Cycloalkyl, more preferably C 5-6 Cycloalkyl, etc.), aryl (e.g., phenyl, tolyl, xylyl, naphthyl, etc. C 6-14 Aryl, preferably C 6-10 Aryl, more preferably C 6-8 Aryl, etc.), aralkyl (benzyl, phenethyl, etc. C 6-10 Aryl-C 1-4 alkyl, etc.) and other monovalent hydrocarbon groups; hydroxyl groups; alkoxy groups (methoxy, ethoxy, propoxy, butoxy, etc. C 1-12 Alkoxy, preferably C 1-8 Alkoxy, more preferably C 1-6 Alkoxy, etc.), cycloalkoxy (cyclohexyloxy, etc. C 5-10 Cycloalkoxy, etc.), aryloxy (phenoxy, etc. C 6-10 aryloxy), aralkyloxy (for example, benzyloxy, etc. C 6-10 Aryl-C 1-4 Alkyloxy) etc. -OR4a The group shown [wherein, R 4a represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above).]; alkylthio group (methylthio, ethylthio, propylthio, butylthio, etc., C 1-12 alkylthio group, preferably C 1-8 alkylthio group, more preferably C 1-6 alkylthio group, etc.), cycloalkylthio group (such as cyclohexylthio, C 5-10 cycloalkylthio group, etc.), arylthio group (such as phenylthio, C 6-10 arylthio group), aralkylthio group (for example, benzylthio, etc., C 6-10 aryl-C 1-4 [[ID=I7]]alkylthio group), etc., -SR 4b The group shown [wherein, R 4b represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above).]; acyl group (such as acetyl, C 1-6 acyl group, etc.); alkoxycarbonyl group (such as methoxycarbonyl, C 1-4 alkoxy-carbonyl group, etc.); halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.); nitro group; cyano group; mercapto group; carboxyl group; amino group; carbamoyl group; alkylamino group (such as methylamino, ethylamino, propylamino, butylamino, etc., C 1-12 alkylamino group, preferably C 1-8 alkylamino group, more preferably C 1-6 alkylamino group, etc.), cycloalkylamino group (such as cyclohexylamino, C 5-10 cycloalkylamino group, etc.), arylamino group (such as phenylamino, C 6-10 arylamino group), aralkylamino group (for example, benzylamino, etc., C 6-10 aryl-C 1-4 alkylamino group), etc., -NHR 4c The group shown [wherein, R 4c represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above).]; dialkylamino group (such as dimethylamino, diethylamino, dipropylamino, dibutylamino, etc., bis(C 1-12 alkyl)amino group, preferably bis(C 1-8 alkyl)amino group, more preferably bis(C 1-6 alkyl)amino group, etc.), dicycloalkylamino group (such as dicyclohexylamino, bis(C [[ID=5B]] 5-10 cycloalkyl)amino group, etc.), diarylamino group (such as diphenylamino, bis(C 6-10 aryl)amino group), diarylalkylamino group (for example, dibenzylamino, etc., bis(C 6-10 aryl-C 1-4 alkyl)amino group), etc., -N(R 4d )2 The group shown [wherein, R 4dIndependently represents a monovalent hydrocarbon group (such as the monovalent hydrocarbon groups exemplified above); (meth)acryloyloxy; sulfo; and the above-mentioned monovalent hydrocarbon group, -OR 4a the group shown; -SR 4b the group shown; acyl; alkoxycarbonyl; -NHR 4c the group shown or -N(R 4d )2 the group shown in which at least a part of the hydrogen atoms bonded to the carbon atoms contained in the group are substituted with the above-mentioned monovalent hydrocarbon group, hydroxyl group, -OR 4a the group shown; -SR 4b the group shown; acyl; alkoxycarbonyl; halogen atom; nitro group; cyano group; mercapto group; carboxyl group; amino group; carbamoyl group; -NHR 4c the group shown; -N(R 4d )2 the group shown; (meth)acryloyloxy; methanesulfonyloxy or sulfo-substituted group [for example, alkoxyaryl (such as methoxyphenyl, etc., C 1-4 alkoxy C 6-10 aryl), alkoxycarbonylaryl (such as methoxycarbonylphenyl, ethoxycarbonylphenyl, etc., C 1-4 alkoxy-carbonyl C 6-10 aryl, etc.)].

[0417] Among them, typically, R 2 can be a monovalent hydrocarbon group, -OR 4a the group shown; -SR 4b the group shown; acyl; alkoxycarbonyl; halogen atom; nitro group; cyano group; -NHR 4c the group shown; -N(R 4d )2 the group shown, etc.

[0418] As a preferred R 2 , examples include a monovalent hydrocarbon group [for example, alkyl group (such as C 1-6 alkyl group), cycloalkyl group (such as C 5-8 cycloalkyl group), aryl group (such as C 6-10 aryl group), aralkyl group (such as C 6-8 aryl-C 1-2 alkyl group), etc.], alkoxy group (C 1-4 alkoxy group, etc.). Particularly preferably, R 2a and R 2b are alkyl groups [C 1-4 alkyl groups (especially methyl group), etc.], aryl groups [such as C 6-10 aryl groups (especially phenyl group), etc.], etc. monovalent hydrocarbon groups (especially alkyl groups).

[0419] It should be noted that when m is an integer of 2 or more, multiple R 2may be different from each other or the same. Additionally, W 1 the R contained in 2 and W 2 the R contained in 2 may be the same or different.

[0420] In formula (b2-1), the number m of R 2 can be selected according to the type of ring Z. For example, it can be 0 or more and 4 or less, preferably 0 or more and 3 or less, more preferably 0 or more and 2 or less. It should be noted that the m in W 1 and the m in W 2 may be the same or different.

[0421] In the above formula (b2-1), R 3 is a group represented by -CO-NH-X b4 -NCO, thiirane-2-ylmethyl or glycidyl. Among these groups, thiirane-2-ylmethyl and glycidyl are preferred. Regarding the group represented by -CO-NH-X b4 -NCO, it is the same as the group represented by -O-CO-NH-X b4 -NCO described above for formula (b1).

[0422] W 1 the R contained in 3 and W 2 the R contained in 3 may be the same or different. Preferably, the R contained in W 1 and the R contained in W 3 and W 2 the R contained in 3 both are thiirane-2-ylmethyl or glycidyl, and more preferably both are the same group selected from the group consisting of thiirane-2-ylmethyl and glycidyl.

[0423] In the above formula (b2), as ring Y 1 and ring Y 2 , for example, a benzene ring, a condensed polycyclic aromatic hydrocarbon ring [for example, a fused bicyclic hydrocarbon ring (for example, a naphthalene ring, etc., a C 8-20 fused bicyclic hydrocarbon ring, preferably a C 10-16 fused bicyclic hydrocarbon ring), a fused tricyclic aromatic hydrocarbon ring (for example, an anthracene ring, a phenanthrene ring, etc.) and other fused 2- to 4-ring aromatic hydrocarbon rings] etc. Ring Y 1 and ring Y 2 are preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring. It should be noted that ring Y 1 and ring Y 2 may be the same or different. For example, one ring can be a benzene ring and the other ring can be a naphthalene ring, etc.

[0424] In the above formula (b2), as R 3a and R 3b , non-reactive substituents are generally cited, such as a cyano group, a halogen atom (fluorine atom, chlorine atom, bromine atom, etc.), a monovalent hydrocarbon group [for example, an alkyl group, an aryl group (such as a phenyl group, a C 6-10 aryl group), etc.], etc. A cyano group or an alkyl group is preferred, and an alkyl group is particularly preferred. As the alkyl group, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc. C 1-6 alkyl groups (such as a C 1-4 alkyl group, particularly methyl) can be exemplified. It should be noted that when t1 is an integer of 2 or more, R 3a can be different from each other or the same. In addition, when t2 is an integer of 2 or more, R 3b can be different from each other or the same. Further, R 3a and R 3b can be the same or different. In addition, regarding the bonding positions (substitution positions) of R 1 and R 2 on the ring Y 3a and the ring Y 3b , there is no particular limitation. The preferred substitution numbers t1 and t2 are 0 or 1, particularly 0. It should be noted that t1 and t2 can be the same as each other or different.

[0425] Among the compounds represented by the above formula (b2), as particularly preferred specific examples, 9,9-bis[4-[2-(glycidyloxy)ethoxy]phenyl]-9H-fluorene, 9,9-bis[4-[2-(glycidyloxy)ethyl]phenyl]-9H-fluorene, 9,9-bis[4-(glycidyloxy)-3-methylphenyl]-9H-fluorene, 9,9-bis[4-(glycidyloxy)-3,5-dimethylphenyl]-9H-fluorene, 9,9-bis(6-glycidyloxynaphthalen-1-yl)-9H-fluorene, 9,9-bis(5-glycidyloxynaphthalen-2-yl)-9H-fluorene and other fluorene compounds containing an epoxy group can be cited; and compounds represented by the following formula.

[0426] [Chemical formula 33]

[0427]

[0428] [Chemical formula 34]

[0429]

[0430] [Chemical formula 35]

[0431]

[0432] [Chemical formula 36]

[0433]

[0434] [Chemical formula 37]

[0435]

[0436] [Crosslinkable binaphthalene compound (Bi-3)]

[0437] As the crosslinkable binaphthalene compound (Bi-3), it is preferably a compound obtained by bonding two or more groups selected from -O-CO-NH-X b4 -NCO-represented groups, glycidyloxy groups, and thietan-2-ylmethyloxy groups to binaphthalenes such as 1,1'-binaphthalene. -O-CO-NH-X b4 Among the -NCO-represented groups, glycidyloxy groups, and thietan-2-ylmethyloxy groups, glycidyloxy groups and thietan-2-ylmethyloxy groups are preferred.

[0438] Regarding -O-CO-NH-X b4 The -NCO-represented group is the same as the -O-CO-NH-X b4 -NCO-represented group described above for formula (b1).

[0439] The number of groups selected from glycidyloxy groups and thietan-2-ylmethyloxy groups possessed by the crosslinkable binaphthalene compound (Bi-3) is preferably 2 or more and 4 or less, more preferably 2 or 3, and still more preferably 2.

[0440] As preferred specific examples of the crosslinkable binaphthalene compound (B3), 2,2'-diglycidyloxy-1,1'-binaphthalene, 2,2'-diglycidyloxy-3,3'-diglycidyloxycarbonyl-1,1'-binaphthalene, 2,2'-diglycidyloxy-6,6'-diglycidyloxycarbonyl-1,1'-binaphthalene, 2,2'-bis(thietan-2-ylmethyl)oxy-1,1'-binaphthalene, 2,2'-bis(thietan-2-ylmethyl)oxy-3,3'-bis(thietan-2-ylmethyl)oxycarbonyl-1,1'-binaphthalene, and 2,2'-bis(thietan-2-ylmethyl)oxy-6,6'-bis(thietan-2-ylmethyl)oxycarbonyl-1,1'-binaphthalene can be cited.

[0441] [Sulfur-containing compound (Bii)]

[0442] The sulfur-containing compound (Bii) is a sulfur-containing compound having two or more crosslinkable groups. The crosslinkable groups are as described above. Among them, a compound that does not contain a sulfur atom other than the sulfur atom contained in the episulfide group does not belong to the sulfur-containing compound (Bii).

[0443] As the crosslinkable group of the sulfur-containing compound (Bii), a glycidyl group and a thiirane-2-ylmethyl group are preferable, and a thiirane-2-ylmethyl group is more preferable.

[0444] As a preferable example of the sulfur-containing compound (Bii), a compound represented by the following formula (b4-1) can be cited.

[0445] R b5 -CH2-S-[-(CH2) p -S-] q -CH2-R b5 ···(b4-1)

[0446] In the formula (b4-1), R b5 is a thiirane-2-yl. p is an integer of 0 or more and 4 or less. q is an integer of 0 or more and 2 or less.

[0447] As a specific example of the compound represented by the formula (b4-1), bis(thiirane-2-ylmethyl) sulfide, bis(thiirane-2-ylmethyl) methane, 1,2-bis(thiirane-2-ylmethyl) ethane, 1,3-bis(thiirane-2-ylmethyl) propane, 1,4-bis(thiirane-2-ylmethyl) butane, and bis(thiirane-2-ylmethylthioethyl) sulfide can be cited.

[0448] As a preferable example of the sulfur-containing compound (Bii), a compound represented by the following formula (b4-2) can be cited.<0s-

[0449] R b5 -CH2-S-(CH2) r -CHX-(CH2) s -S-CH2-R b5 ···(b4-2)

[0450] In the formula (b4-2), R b5 is a thiirane-2-yl. CHX is a cyclohexanediyl. r and s are each independently an integer of 0 or more and 4 or less.

[0451] As specific examples of the compound represented by the formula (b4-2), 1,3-bis(thiirane-2-ylmethylthio)cyclohexane, 1,4-bis(thiirane-2-ylmethylthio)cyclohexane, 1,3-bis(thiirane-2-ylmethylthiomethyl)cyclohexane, and 1,4-bis(thiirane-2-ylmethylthiomethyl)cyclohexane can be mentioned.

[0452] As a preferred example of the sulfur-containing compound (Bii), a compound represented by the following formula (b4-3) can be mentioned.

[0453] R b5 -CH2-S-(CH2) t -DTA-(CH2) u -S-CH2-R b5 ···(b4-3)

[0454] In the formula (b4-3), R b5 is a thiirane-2-yl. DTA is a 1,4-dithiane diyl. t and u are each independently an integer of 0 or more and 4 or less.

[0455] As specific examples of the compound represented by the formula (b4-3), 2,5-bis(thiirane-2-ylmethylthio)-1,4-dithiane, and 2,5-bis(thiirane-2-ylmethylthiomethyl)-1,4-dithiane can be mentioned.

[0456] As a preferred example of the sulfur-containing compound (Bii), a compound represented by the following formula (b4-4) can be mentioned.

[0457] R b5 -CH2-S-(CH2) v -Ph-(CH2) w -S-CH2-R b5 ···(b4-4)

[0458] In the formula (b4-4), R b5 is a thiirane-2-yl. Ph is a phenylene group. v and w are each independently an integer of 0 or more and 4 or less.

[0459] As specific examples of the compound represented by the formula (b4-4), 1,3-bis(thiirane-2-ylmethylthio)benzene, 1,4-bis(thiirane-2-ylmethylthio)benzene, 1,3-bis(thiirane-2-ylmethylthiomethyl)benzene, and 1,4-bis(thiirane-2-ylmethylthiomethyl)benzene can be mentioned.

[0460] 〔Isocyanate compound (Biii)〕

[0461] The isocyanate compound (Biii) is a compound having two or more isocyanate groups in one molecule. The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii).

[0462] From the viewpoint of good temporal stability of the non-photosensitive liquid composition, the isocyanate compound (Biii) is preferably used in the form of a blocked isocyanate compound obtained by reacting with a known blocking agent. In the blocked isocyanate compound, the highly reactive isocyanate group is blocked by the blocking agent, and thus, the non-photosensitive liquid composition containing the blocked isocyanate compound has good temporal stability.

[0463] The isocyanate compound (Biii) is not particularly limited as long as it is a compound having two or more isocyanate groups. Known isocyanate compounds (Biii) include chain aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and their modified polyisocyanates. The aromatic polyisocyanate is a polyisocyanate having an aromatic group. In the aromatic polyisocyanate, the isocyanate group may be bonded to the aromatic group or to the aliphatic group.

[0464] These isocyanate compounds (Biii) may be used alone or in combination of two or more.

[0465] Examples of the chain aliphatic polyisocyanate include 1,4-butane diisocyanate, 1,6-hexane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and dimer acid diisocyanate.

[0466] Examples of the alicyclic polyisocyanate include 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexane (isophorone diisocyanate), bis(4-isocyanatocyclohexyl)methane, and norbornane diisocyanate.

[0467] Examples of the aromatic polyisocyanate having an isocyanate group bonded to the aromatic group include 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, crude diphenylmethane diisocyanate, 1,4-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 3,3'-dimethyl-4,4'-diisocyanatodiphenylmethane, and 1,5-naphthalene diisocyanate.

[0468] Examples of the aromatic polyisocyanate having an isocyanate group bonded to an aliphatic group include 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, α,α,α’,α’-tetramethylphenylene diisocyanate, and the like.

[0469] Examples of the blocking agent include alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, 2-ethylhexanol, and butyl cellosolve; phenols such as phenol, cresol, and 2-hydroxypyridine; amines such as diisopropylamine; lactams such as ε-caprolactam, δ-valerolactam, and γ-butyrolactam; oximes such as formaldehyde oxime, acetaldehyde oxime, acetone oxime, methyl ethyl ketone oxime, and methyl isobutyl ketone oxime; ketene alcohols such as acetylacetone; pyrazoles such as 1,2-pyrazole and 3,5-dimethylpyrazole; triazoles such as triazole, and the like.

[0470] Among these blocking agents, lactams, oximes, and pyrazoles are preferred, and ε-caprolactam, methyl ethyl ketone oxime, and 3,5-dimethylpyrazole are more preferred.

[0471] [Aliphatic compound (Biv)]

[0472] The aliphatic compound (Biv) is an aliphatic compound containing two or more crosslinkable groups. The aliphatic compound (Biv) is a compound that does not belong to the sulfur-containing compound (Bii) and the isocyanate compound (Biii).

[0473] The structure of the aliphatic compound (Biv) can be a chain structure, a cyclic structure, or a combination of a chain structure and a cyclic structure.

[0474] As the crosslinkable group of the aliphatic compound (Biv), a glycidyl group and a thiirane-2-ylmethyl group are preferred.

[0475] Examples of the aliphatic compound (Biv) include compounds obtained by substituting hydrogen atoms in two or more of the hydroxyl groups in various aliphatic polyols with a glycidyl group or a thiirane-2-ylmethyl group.

[0476] Preferred examples of the polyol that can supply the aliphatic compound (Biv) include ethylene glycol, 1,2-propanediol (propane-1,2-diol), propane-1,3-diol, butane-1,4-diol, pentane-1,5-diol, hexane-1,6-diol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, glycerol, diglycerol, triglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, 1,4-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, sorbitol, and isosorbitol, and the like.

[0477] As preferred specific examples of the aliphatic compound (Biv) having an epoxy group, there may be mentioned ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, propane-1,3-diol diglycidyl ether, butane-1,4-diol diglycidyl ether, pentane-1,5-diol diglycidyl ether, hexane-1,6-diol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, glycerol-1,3-diglycidyl ether, glycerol-1,2-diglycidyl ether, diglycerol diglycidyl ether, diglycerol triglycidyl ether, diglycerol tetraglycidyl ether, triglycerol diglycidyl ether, triglycerol triglycidyl ether, triglycerol tetraglycidyl ether, triglycerol pentaglycidyl ether, triglycerol, triglycerol hexaglycidyl ether, trimethylolpropane diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol diglycidyl ether, pentaerythritol triglycidyl ether, pentaerythritol tetraglycidyl ether, dipentaerythritol diglycidyl ether, dipentaerythritol triglycidyl ether, dipentaerythritol tetraglycidyl ether, dipentaerythritol pentaglycidyl ether, dipentaerythritol hexaglycidyl ether, 1,4-cyclohexanediol diglycidyl ether, 1,3-cyclohexanediol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,3-cyclohexanedimethanol diglycidyl ether, sorbitol diglycidyl ether, sorbitol triglycidyl ether, sorbitol tetraglycidyl ether, sorbitol pentaglycidyl ether, sorbitol hexaglycidyl ether, and isosorbitol diglycidyl ether, etc.

[0478] As preferred specific examples of the aliphatic compound (Biv) having a thiirane group, there may be mentioned compounds obtained by replacing the glycidyl group with a thiiran-2-ylmethyl group in the compounds described above as specific examples of the aliphatic compound (Biv) having an epoxy group.

[0479] The amount of the crosslinkable compound (B) used in the non-photosensitive liquid composition is not particularly limited as long as the desired effects are not impaired. From the viewpoints of good curability of the non-photosensitive liquid composition and excellent solvent resistance of the cured product, the amount of the crosslinkable compound (B) used in the non-photosensitive liquid composition is preferably 10 parts by mass or more and 200 parts by mass or less, more preferably 30 parts by mass or more and 150 parts by mass or less, relative to 100 parts by mass of the polymer (1A).

[0480] 〔Organic solvent (S)〕

[0481] As the organic solvent (S), a solvent capable of dissolving the polymer (1A) is preferably used. Examples of the organic solvent (S) include nitrogen-containing polar organic solvents such as N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylformamide, N-methylformamide, N,N-dimethylpropanamide, N,N-dimethylisobutyramide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-methyl-2-piperidone, N-acetylpyrrolidine, N,N'-dimethylethyleneurea (1,3-dimethyl-2-imidazolidinone), N,N'-dimethylpropyleneurea, N,N,N',N'-tetramethylpropanediamide, N-methylcaprolactam, N,N,N',N'-tetramethylurea, 3-methoxy-N,N-dimethylpropanamide, and 3-butoxy-N,N-dimethylpropanamide; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, cyclopentanone, and cyclohexanone; ethers such as tetrahydrofuran and 1,4-dioxane; aromatic hydrocarbons such as toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, and styrene; monoalkyl ether acetates of diols such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and diethylene glycol monoethyl ether acetate; monoalkyl ethers of diols such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, and 1-methoxy-2-butanol; dialkyl ethers of diols such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and triethylene glycol dimethyl ether; diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, hexanediol, and diethylene glycol; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, 1-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 2-methyl-1-pentanol, 1-octanol, 2-ethylhexanol, allyl alcohol, cyclohexanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, and benzyl alcohol; esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, and isobutyl acetate; and lactones such as γ-butyrolactone.

[0482] From the viewpoint that the polymer (1A) is easily and particularly well dissolved, the organic solvent (S) preferably contains a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a diol, or a monoalkyl ether of a diol.

[0483] Regarding the amount of the organic solvent (S) used, it is not particularly limited as long as the non-photosensitive liquid composition can be formed into a desired shape. The organic solvent (S) is used in such a manner that the solid content concentration of the non-photosensitive liquid composition is preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 40% by mass or less.

[0484] 〔Thermal acid generator (C)〕

[0485] When the polymer (A) has a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group as R a1 the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0486] As the thermal acid generator (C), there is no particular limitation as long as it is a compound that generates an acid upon heating. As the thermal acid generator (C), known thermal acid generators can be appropriately selected.

[0487] As the thermal acid generator (C), from the viewpoint of the acid generating ability based on heating, an onium salt type thermal acid generator is preferred. As the onium salt, sulfonium ions, ammonium ions, iodonium ions, and phosphonium ions can be mentioned. They are preferred because they are stable and easy to handle. Among these onium salts, sulfonium ions and iodonium ions are more preferred, and sulfonium ions are even more preferred.

[0488] The amount of the thermal acid generator (C) used is not particularly limited as long as the desired effects are not impaired. Relative to the mass of the solid content of the non-photosensitive liquid composition, the amount of the thermal acid generator (C) used is preferably 0.1% by mass or more and 15% by mass or less, more preferably 0.5% by mass or more and 10% by mass or less.

[0489] 〔Surfactant (D)〕

[0490] The non-photosensitive liquid composition may further contain a surfactant (surface conditioner) (D) in order to improve film forming properties, coating properties, defoaming properties, leveling properties, etc. The surfactant can be used alone as one kind, or two or more kinds can be used in combination. As the surfactant, for example, silicone-based surfactants, fluorine-based surfactants, and polymer wetting and dispersing agents can be mentioned. In particular, from the viewpoint of improving film forming properties, a polymer wetting and dispersing agent is preferred.

[0491] As silicone-based surfactants, specifically, BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341, BYK-344, BYK-345, BYK-346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 (manufactured by BYK Chemie) etc. can be cited.

[0492] As fluorine-based surfactants, specifically, F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF-1132, TF-1027SF, TF-1441, TF-1442 (manufactured by DIC); PF-636, PF-6320, PF-656, PF-6520 of PolyFox series (manufactured by Omnova) etc. can be cited.

[0493] As polymer wetting and dispersing agents, specifically, BYK-140, BYK-145, BYK-161, BYK-162, BYK-163, BYK-164, BYK-167, BYK-168, BYK-170, BYK-171, BYK-174, BYK-180, BYK-182, BYK-184, BYK-185, BYK-2050, BYK-2055, BYK-2015, BYK-9077 (manufactured by BYK Chemie) etc. can be cited.

[0494] The amount of surfactant (D) used is not particularly limited. Considering aspects such as the film-forming property, coatability, defoaming property, and leveling property of the non-photosensitive liquid composition, the amount of surfactant (D) used is preferably 0.01% by mass or more and 2% by mass or less, more preferably 0.05% by mass or more and 1% by mass or less, relative to the mass of the solid components of the non-photosensitive liquid composition.

[0495] 〔Other components〕

[0496] The non-photosensitive liquid composition may contain additives such as defoamers, silane coupling agents, colorants (pigments, dyes), and crosslinking agents as needed. Any additives can use conventionally known compounds.

[0497] 〔Manufacturing method of non-photosensitive liquid composition〕

[0498] The non-photosensitive liquid composition can be manufactured by the following method: After mixing any components as needed into the essential components described above, each component is uniformly dissolved in the organic solvent (S). The non-photosensitive liquid composition can also be filtered through a filter with a desired mesh size as needed.

[0499] <Manufacturing method of molded body>

[0500] A method including the following steps can be used to manufacture a molded body:

[0501] A step of molding the aforementioned non-photosensitive liquid composition; and

[0502] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0503] As the molding method, there is no particular limitation, and it can be appropriately selected according to the shape of the molded body. As the molding method, for example, coating, casting into a mold, etc. can be cited. In addition, the so-called 3D printing method can also be used to mold the non-photosensitive liquid composition into a desired three-dimensional shape.

[0504] Hereinafter, as a representative example of the manufacturing method of the molded body, the manufacturing method of a film will be described.

[0505] First, the non-photosensitive liquid composition is coated on a desired substrate to form a coating film.

[0506] The method of coating the non-photosensitive liquid composition on the substrate is not particularly limited. For example, contact transfer type coating devices such as a roll coater, reverse roll coater, bar coater, and slot coater, and non-contact type coating devices such as a spinner (rotary coating device) and a curtain coater can be used to coat the non-photosensitive liquid composition on the substrate so as to have a desired film thickness, thereby forming a coating film.

[0507] Next, the coated film is heated to remove the organic solvent (S) from the coated film. The heating temperature can be appropriately determined according to the boiling point of the organic solvent (S), the temperature at which the acid generator (C) generates acid, and the like.

[0508] The temperature for heating the coated film is preferably, for example, 100°C or higher and 400°C or lower, more preferably 150°C or higher and 300°C or lower. The heating time is preferably 30 seconds or longer and 30 minutes or shorter, more preferably 1 minute or longer and 20 minutes or shorter.

[0509] The molded body thus obtained exhibits a high refractive index. Specifically, the refractive index of the molded body, measured with respect to the refractive index of light having a wavelength of 550 nm, is preferably 1.74 or higher, more preferably 1.75 or higher.

[0510] Such a molded body exhibiting a high refractive index can be suitably used as various optical components. The optical component is preferably a film or a microlens. The optical component formed from the molded body of the non-photosensitive liquid composition can be suitably used in various optical elements. The molded body as a film can be used as a high refractive index film in various optical elements. The molded body as a microlens can be particularly suitably used in optical elements such as CCD and CMOS.

[0511] <<Second Embodiment>>

[0512] <Polymer (2A) containing a triazine ring>

[0513] The polymer (2A) containing a triazine ring contains a structural unit represented by the following formula (A1). The polymer (2A) containing a triazine ring may also contain other structural units in addition to the structural unit represented by the following formula (A1). As the other structural unit, a structural unit represented by the following formula (A2) is preferred.

[0514] Hereinafter, the polymer (2A) containing a triazine ring is also referred to as "polymer (2A)".

[0515] The polymer (2A) has a group represented by the following formula (A1-1) at at least a part of the molecular chain ends.

[0516] -X 2 -X 3 -X 4 ···(A1-1)

[0517] (In formula (A1-1), X 2 is the same as X in formula (A1) 2 and,

[0518] X 3 is a divalent hydrocarbon group,

[0519] X4 is -OR a3 or -N(R a3 )2,

[0520] R a3 is a hydrogen atom or an alkyl group which may have substituents,

[0521] When the hydrocarbon group as X 3 is a group containing an aromatic group, X 4 is not an amino group.)

[0522] The above-mentioned polymer (2A) exhibits a high refractive index, and even when exposed to high temperature for a long time, the light transmittance is not easily reduced.

[0523] Hereinafter, the structural unit represented by the formula (A1) will also be referred to as "unit (A1)". The structural unit represented by the formula (A2) will also be referred to as "unit (A2)". <&

[0524] [Chemical formula 38]

[0525]

[0526] In the formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group. R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group. The acetal protecting group is a group represented by -CHR A1 -O-R A2 R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may be bonded to each other to form a ring; X 1 and X 2 are each independently -NR a2 -, -O- or -S-; R a2 is a hydrogen atom, an alkyl group which may have substituents, or an aromatic hydrocarbon group which may have substituents; X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 1 ; X 2 is bonded to an aromatic ring in the group containing an aromatic group as Ar 2 .

[0527] [Chemical formula 39]

[0528]

[0529] In the formula (A2), Ar2 and Ar 3 is a group containing an aromatic group. X 1 and X 2 are each independently -NR a2 -, -O- or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 3 is bonded to an aromatic ring in the group containing an aromatic group as Ar 2 is bonded to an aromatic ring in the group containing an aromatic group as Ar 2 is bonded to an aromatic ring in the group containing an aromatic group as Ar.

[0530] The polymer (2A) containing the unit (A1) has a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group.

[0531] The above polymer (2A) is soluble in various organic solvents such as nitrogen-containing polar organic solvents and ketone solvents.

[0532] However, by deprotecting the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or by deprotecting the carboxyl group protected with an acid dissociable group, the above polymer (2A) becomes poorly soluble in organic solvents. The deprotected polymer having a hydroxyl group, an amino group, or a carboxyl group can be crosslinked with a polymerizable monomer capable of reacting with the hydroxyl group, the amino group, or the carboxyl group, and thus becomes more poorly soluble in organic solvents. As the polymerizable monomer, a crosslinkable compound (B) described later can be mentioned.

[0533] Therefore, the above polymer (2A) is easily processed as a solution. On the other hand, a molded article produced using a solution of the aforementioned polymer (2A) under conditions for deprotecting the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or the carboxyl group protected with an acid dissociable group is poorly soluble in organic solvents.

[0534] The ratio of the mass of the unit (A1) to the mass of the polymer (2A) is not particularly limited within a range that does not impair the desired effect. Regarding the ratio of the mass of the unit (A1) to the mass of the polymer, it can be 10% by mass or more, 20% by mass or more, 30% by mass or more, 50% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 100% by mass with respect to the mass of the polymer (2A).

[0535] When the polymer (2A) contains the unit (A1) and the unit (A2), the ratio of the number of moles of the unit (A1) to the total number of moles of the unit (A1) and the unit (A2) is preferably 10 mol% or more and 70 mol% or less, more preferably 20 mol% or more and 70 mol% or less, and particularly preferably 30 mol% or more and 60 mol% or less.

[0536] 〔Unit (A1)〕

[0537] The unit (A1) is the unit represented by the aforementioned formula (A1). The formula (A1) is the same as the formula (A1) described for the first embodiment. That is, the unit (A1) is the same as the unit (A1) possessed by the triazine ring-containing polymer (A1) related to the first embodiment.

[0538] 〔Unit (A2)〕

[0539] As described above, the polymer (2A) may also contain the unit (A2) as other structural units in addition to the unit (A1).

[0540] The unit (A2) is the unit represented by the aforementioned formula (A2). The formula (A2) is the same as the formula (A2) described for the first embodiment. That is, the unit (A2) is the same as the unit (A2) possessed by the triazine ring-containing polymer (A1) related to the first embodiment.

[0541] The polymer (2A) has a group represented by the following formula (A1-1) at at least a part of the molecular chain end.

[0542] -X 2 -X 3 -X 4 ···(A1-1)

[0543] In the formula (A1-1), X 2 is the same as X 2 in the formula (A1). X 3 is a divalent hydrocarbon group. X 4 is -OR a3 or -N(R a3 )2. R a3 is a hydrogen atom or an alkyl group which may have a substituent. In -N(R a3 )2, the two Rs a3 may be the same or different. Preferably, one of the two Rs a3 is a hydrogen atom. When the hydrocarbon group as X 3 contains an aromatic group, X 4 is not an amino group.

[0544] In the formula (A1-1), as X 3 ​​​​​​​​​​​​​​​​​​The type and number of carbon atoms of the divalent hydrocarbon group are not particularly limited as long as the desired effects are not impaired. As X 3 The divalent hydrocarbon group may be an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group.

[0545] As X 3 The number of carbon atoms of the divalent hydrocarbon group is preferably 1 or more and 20 or less, more preferably 1 or more and 16 or less, and further preferably 1 or more and 12 or less.

[0546] Regarding the preferred examples of the aliphatic hydrocarbon group when the divalent hydrocarbon group as X 3 is an aliphatic hydrocarbon group, examples thereof include methylene, ethane-1,2-diyl, ethane-1,1-diyl, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, and decane-1,10-diyl.

[0547] Regarding the preferred examples of the hydrocarbon group when the divalent hydrocarbon group as X 3 is an aromatic hydrocarbon group, examples thereof include p-phenylene, m-phenylene, o-phenylene, naphthalene-1,4-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, biphenyl-4,4'-diyl, and biphenyl-3,4'-diyl.

[0548] Regarding the preferred examples of the divalent hydrocarbon group when the divalent hydrocarbon group as X 3 is a combination of an aliphatic hydrocarbon group and an aromatic hydrocarbon group, examples thereof include -CH2-pPh-, -CH2-mPh-, -CH2-oPh-, -CH2CH2-pPh-, -CH2CH2-mPh-, -CH2CH2-oPh-, -pPh-CH2-pPh-, -mPh-CH2-mPh-, -pPh-CH2-mPh-, -pPh-C(CH3)2-pPh-, -mPh-C(CH3)2-mPh-, and -pPh-C(CH3)2-mPh-. pPh is p-phenylene. mPh is m-phenylene. oPh is o-phenylene.

[0549] As R in X 4 a3The alkyl group may have substituents. Examples of the substituents that the alkyl group may have include a hydroxyl group; a mercapto group; alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, and a n-butoxy group; alkylthio groups such as a methylthio group, an ethylthio group, a n-propylthio group, an isopropylthio group, and a n-butylthio group; an amino group; monosubstituted amino groups such as a methylamino group, an ethylamino group, a n-propylamino group, an isopropylamino group, a n-butylamino group, a 2-hydroxyethylamino group, and a 3-hydroxypropylamino group; disubstituted amino groups such as a dimethylamino group, a diethylamino group, a di-n-propylamino group, a diisopropylamino group, a di-n-butylamino group, an N-methyl-N-ethylamino group, an N-methyl-N-(2-hydroxyethyl)amino group, an N-ethyl-N-(2-hydroxyethyl)amino group, and a bis(2-hydroxyethyl)amino group; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; and a cyano group, etc.

[0550] As R a3 There is no particular limitation on the number of carbon atoms of the alkyl group. As R a3 The number of carbon atoms of the alkyl group is preferably 1 or more and 20 or less, more preferably 1 or more and 12 or less, still more preferably 1 or more and 8 or less, and particularly preferably 1 or more and 4 or less.

[0551] Regarding specific examples of the alkyl group as R a3 Examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a n-hexyl group, a n-heptyl group, a n-octyl group, a n-ethylhexyl group, a n-nonyl group, a n-decyl group, a n-undecyl group, a n-dodecyl group, a n-tridecyl group, a n-tetradecyl group, a n-pentadecyl group, a n-hexadecyl group, a n-heptadecyl group, a n-octadecyl group, a n-nonadecyl group, and a icosyl group, etc.

[0552] Preferred examples of the group represented by the above formula (A1-1) include:

[0553] Hydroxyalkylamines such as 2-hydroxyethylamine, 3-hydroxypropylamine, and 4-hydroxybutylamine;

[0554] Hydroxyalkyloxies such as 2-hydroxyethyloxy, 3-hydroxypropyloxy, and 4-hydroxybutyloxy;

[0555] Hydroxyalkylthios such as 2-hydroxyethylthio, 3-hydroxypropylthio, and 4-hydroxybutylthio;

[0556] Alkoxyalkylamines such as 2-methoxyethylamine, 3-methoxypropylamine, and 4-methoxybutylamine;

[0557] Alkoxyalkyloxies such as 2-methoxyethyloxy, 3-methoxypropyloxy, and 4-methoxybutyloxy;

[0558] Alkoxyalkylthio groups such as 2-methoxyethylthio, 3-methoxypropylthio, and 4-methoxybutylthio;

[0559] Aminoalkylamino groups such as 2-aminoethylamino, 3-aminopropylamino, and 4-aminobutylamino;

[0560] Aminoalkyloxy groups such as 2-aminoethyloxy, 3-aminopropyloxy, and 4-aminobutyloxy;

[0561] Aminoalkylthio groups such as 2-aminoethylthio, 3-aminopropylthio, and 4-aminobutylthio;

[0562] Alkylaminoalkylamino groups such as 2-methylaminoethylamino, 3-methylaminopropylamino, 4-methylaminobutylamino, 2-ethylaminoethylamino, 3-ethylaminopropylamino, and 4-ethylaminobutylamino;

[0563] Alkylaminoalkyloxy groups such as 2-methylaminoethyloxy, 3-methylaminopropyloxy, 4-methylaminobutyloxy, 2-ethylaminoethyloxy, 3-ethylaminopropyloxy, and 4-ethylaminobutyloxy;

[0564] Alkylaminoalkylthio groups such as 2-methylaminoethylthio, 3-methylaminopropylthio, 4-methylaminobutylthio, 2-ethylaminoethylthio, 3-ethylaminopropylthio, and 4-ethylaminobutylthio;

[0565] Hydroxyalkylaminoalkylamino groups such as 2-(2-hydroxyethylamino)ethylamino, 3-(2-hydroxyethylamino)propylamino, and 4-(2-hydroxyethylamino)butylamino;

[0566] Hydroxyalkylaminoalkyloxy groups such as 2-(2-hydroxyethylamino)ethyloxy, 3-(2-hydroxyethylamino)propyloxy, and 4-(2-hydroxyethylamino)butyloxy;

[0567] Hydroxyalkylaminoalkylthio groups such as 2-(2-hydroxyethylamino)ethylthio, 3-(2-hydroxyethylamino)propylthio, and 4-(2-hydroxyethylamino)butylthio;

[0568] Disubstituted aminoalkyl alkylamines such as 2-dimethylaminoethylamino, 3-dimethylaminopropylamino, 4-dimethylaminobutylamino, 2-diethylaminoethylamino, 3-diethylaminopropylamino, 4-diethylaminobutylamino, 2-(N-methyl-N-ethylamino)ethylamino, 3-(N-methyl-N-ethylamino)propylamino, 4-(N-methyl-N-ethylamino)butylamino, 2-(N-methyl-N-2-hydroxyethylamino)ethylamino, 3-(N-methyl-N-2-hydroxyethylamino)propylamino, 4-(N-methyl-N-2-hydroxyethylamino)butylamino, 2-(N-ethyl-N-2-hydroxyethylamino)ethylamino, 3-(N-ethyl-N-2-hydroxyethylamino)propylamino, 4-(N-ethyl-N-2-hydroxyethylamino)butylamino, 2-[bis(2-hydroxyethyl)amino]ethylamino, 3-[bis(2-hydroxyethyl)amino]propylamino, and 4-[bis(2-hydroxyethyl)amino]butylamino;

[0569] Disubstituted aminoalkyl alkoxies such as 2-dimethylaminoethyloxy, 3-dimethylaminopropyloxy, 4-dimethylaminobutyloxy, 2-diethylaminoethyloxy, 3-diethylaminopropyloxy, 4-diethylaminobutyloxy, 2-(N-methyl-N-ethylamino)ethyloxy, 3-(N-methyl-N-ethylamino)propyloxy, 4-(N-methyl-N-ethylamino)butyloxy, 2-(N-methyl-N-2-hydroxyethylamino)ethyloxy, 3-(N-methyl-N-2-hydroxyethylamino)propyloxy, 4-(N-methyl-N-2-hydroxyethylamino)butyloxy, 2-(N-ethyl-N-2-hydroxyethylamino)ethyloxy, 3-(N-ethyl-N-2-hydroxyethylamino)propyloxy, 4-(N-ethyl-N-2-hydroxyethylamino)butyloxy, 2-[bis(2-hydroxyethyl)amino]ethyloxy, 3-[bis(2-hydroxyethyl)amino]propyloxy, and 4-[bis(2-hydroxyethyl)amino]butyloxy;

[0570] Disubstituted aminoalkyl alkylthio groups such as 2-dimethylaminoethylthio, 3-dimethylaminopropylthio, 4-dimethylaminobutylthio, 2-diethylaminoethylthio, 3-diethylaminopropylthio, 4-diethylaminobutylthio, 2-(N-methyl-N-ethylamino)ethylthio, 3-(N-methyl-N-ethylamino)propylthio, 4-(N-methyl-N-ethylamino)butylthio, 2-(N-methyl-N-2-hydroxyethylamino)ethylthio, 3-(N-methyl-N-2-hydroxyethylamino)propylthio, 4-(N-methyl-N-2-hydroxyethylamino)butylthio, 2-(N-ethyl-N-2-hydroxyethylamino)ethylthio, 3-(N-ethyl-N-2-hydroxyethylamino)propylthio, 4-(N-ethyl-N-2-hydroxyethylamino)butylthio, 2-[bis(2-hydroxyethyl)amino]ethylthio, 3-[bis(2-hydroxyethyl)amino]propylthio, and 4-[bis(2-hydroxyethyl)amino]butylthio;

[0571] Hydroxyaryl amino groups such as 4-hydroxyphenylamino, 3-hydroxyphenylamino, and 2-hydroxyphenylamino;

[0572] Alkoxyaryl amino groups such as 4-methoxyphenylamino, 3-methoxyphenylamino, and 2-methoxyphenylamino;

[0573] Alkylaminoaryl amino groups such as 4-methylaminophenylamino, 3-methylaminophenylamino, and 2-methylaminophenylamino;

[0574] Hydroxyaryl oxy groups such as 4-hydroxyphenyloxy, 3-hydroxyphenyloxy, and 2-hydroxyphenyloxy;

[0575] Alkoxyaryl oxy groups such as 4-methoxyphenyloxy, 3-methoxyphenyloxy, and 2-methoxyphenyloxy;

[0576] Alkylaminoaryl oxy groups such as 4-methylaminophenyloxy, 3-methylaminophenyloxy, and 2-methylaminophenyloxy;

[0577] Hydroxyaryl thio groups such as 4-hydroxyphenylthio, 3-hydroxyphenylthio, and 2-hydroxyphenylthio;

[0578] Alkoxyaryl thio groups such as 4-methoxyphenylthio, 3-methoxyphenylthio, and 2-methoxyphenylthio;

[0579] Alkylaminoaryl thio groups such as 4-methylaminophenylthio, 3-methylaminophenylthio, and 2-methylaminophenylthio;

[0580] Disubstituted amines such as dimethylamino, diethylamino, methylethylamino, N-methyl-N-(2-hydroxyethyl)amino, N-ethyl-N-(2-hydroxyethyl)amino, and bis(2-hydroxyethyl)amino.

[0581] A method for introducing a group represented by formula (A1-1) into at least a part of the terminal of the molecular chain of polymer (2A) will be described later.

[0582] The weight-average molecular weight of polymer (2A) is not particularly limited as long as the desired effects are not impaired. The weight-average molecular weight is preferably 500 or more and 100,000 or less. From the viewpoint of the high solvent resistance of the polymer in the heated state, the weight-average molecular weight is preferably 2,000 or more. From the viewpoint of the high solubility of the polymer in various solvents, the weight-average molecular weight is preferably 30,000 or less.

[0583] The weight-average molecular weight is the molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0584] [Manufacturing method of polymer (2A)]

[0585] The manufacturing method of polymer (2A) described above is not particularly limited as long as the obtained polymer (2A) has unit (A1) and the terminal group represented by formula (A1-1).

[0586] Typically, the above polymer is manufactured by condensing a dihalotriazine compound with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0587] In addition, the condensation of a dihalotriazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) is carried out in the presence of a compound represented by any one of the following formulas (A7-1) to (A7-3), or the condensation product of a dihalotriazine compound with a compound represented by any one of formulas (A5-1) to (A5-3) is reacted with a compound represented by any one of formulas (A7-1) to (A7-3), whereby a group represented by formula (A1-1) is introduced into the terminal of the molecular chain of the polymer.

[0588] The dihalotriazine compound used for manufacturing polymer (2A) includes a compound represented by the following formula (A3). The compound represented by formula (A3) can supply unit (A1) through condensation with a compound represented by any one of formulas (A5-1) to (A5-3).

[0589] The dihalotriazine compound represented by formula (A3) is the same as the dihalotriazine compound represented by formula (A3) described in the first embodiment.

[0590] When the polymer (2A) contains the unit (A2), the dihalotriazine compound contains a compound represented by the following formula (A6). The compound represented by formula (A6) can supply the unit (A2) by condensation with any one of the compounds represented by formulas (A5-1) to (A5-3).

[0591] [Chemical formula 40]

[0592]

[0593] In formula (A3), Hal is a halogen atom. Ar 1 is a group containing an aromatic group. R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid-dissociable group. The acetal protecting group is -CHR A1 -O-R A2 represents a group. R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may be bonded to each other to form a ring. X 1 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 1 .

[0594] [Chemical formula 41]

[0595]

[0596] In formula (A6), Hal is a halogen atom. Ar 3 is a group containing an aromatic group. X 1 are each independently -NR a2 -, -O-, or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 3 .

[0597] Ar 2 -(NR a2 H)2···(A5-1)

[0598] Ar 2 -(OH)2···(A5-2)

[0599] Ar 2 -(SH)2···(A5-3)

[0600] The aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), and the aromatic dithiol represented by formula (A5-3) are the same as the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), and the aromatic dithiol represented by formula (A5-3) described in relation to the first embodiment.

[0601] X 4 -X 3 -NR a2 H···(A7-1)

[0602] X 4 -X 3 -OH···(A7-2)

[0603] X 4 -X 3 -SH···(A7-3)

[0604] In formulas (A7-1) to (A7-3), X 3 and X 4 and X in formula (A1-1) 3 and X 4 Likewise. a2 and R in formula (A1) a2 same.

[0605] Examples of the compound represented by formula (A7-1) include:

[0606] Hydroxyalkylamines such as 2-hydroxyethylamine, 3-hydroxypropylamine, and 4-hydroxybutylamine;

[0607] Alkoxyalkylamines such as 2-methoxyethylamine, 3-methoxypropylamine, and 4-methoxybutylamine;

[0608] Aminoalkylamines (alkane diamines) such as 2-aminoethylamine (ethylenediamine), 3-aminopropylamine (1,3-diaminopropane), and 4-aminobutylamine (1,4-diaminobutane);

[0609] Alkylaminoalkylamines such as 2-methylaminoethylamine, 3-methylaminopropylamine, 4-methylaminobutylamine, 2-ethylaminoethylamine, 3-ethylaminopropylamine, and 4-ethylaminobutylamine;

[0610] Hydroxyalkylaminoalkylamines such as 2-(2-hydroxyethylamino)ethylamine, 3-(2-hydroxyethylamino)propylamine, 4-(2-hydroxyethylamino)butylamine;

[0611] Disubstituted aminoalkylalkylamines such as (2-aminoethyl)dimethylamine, (3-aminopropyl)dimethylamine, (4-aminobutyl)dimethylamine, (2-aminoethyl)diethylamine, (3-aminopropyl)diethylamine, (4-aminobutyl)diethylamine, 2-(N-methyl-N-ethylamino)ethylamine, 3-(N-methyl-N-ethylamino)propylamine, 4-(N-methyl-N-ethylamino)butylamine, 2-(N-methyl-N-2-hydroxyethylamino)ethylamine, 3-(N-methyl-N-2-hydroxyethylamino)propylamine, 4-(N-methyl-N-2-hydroxyethylamino)butylamine, 2-(N-ethyl-N-2-hydroxyethylamino)ethylamine, 3-(N-ethyl-N-2-hydroxyethylamino)propylamine, 4-(N-ethyl-N-2-hydroxyethylamino)butylamine, 2-[bis(2-hydroxyethyl)amino]ethylamine, 3-[bis(2-hydroxyethyl)amino]propylamine, and 4-[bis(2-hydroxyethyl)amino]butylamine;

[0612] Hydroxyarylamines such as 4-hydroxyaniline, 3-hydroxyaniline, and 2-hydroxyaniline;

[0613] Alkoxyarylamines such as 4-methoxyaniline, 3-methoxyaniline, and 2-methoxyaniline;

[0614] Alkylaminoarylamines such as 4-methylaminoaniline, 3-methylaminoaniline, and 2-methylaminoaniline;

[0615] Hydroxyarylalkylamines such as 4-hydroxybenzylamine, 3-hydroxybenzylamine, 2-hydroxybenzylamine, 4-hydroxy phenethylamine, 3-hydroxy phenethylamine, and 2-hydroxy phenethylamine;

[0616] Alkoxyarylalkylamines such as 4-methoxybenzylamine, 3-methoxybenzylamine, 2-methoxybenzylamine, 4-methoxyphenethylamine, 3-methoxyphenethylamine, and 2-methoxyphenethylamine;

[0617] Aminoarylalkylamines such as 4-aminobenzylamine, 3-aminobenzylamine, 2-aminobenzylamine, 4-aminophenethylamine, 3-aminophenethylamine, and 2-aminophenethylamine;

[0618] Methylaminoarylalkylamines such as 4-methylaminobenzylamine, 3-methylaminobenzylamine, 2-methylaminobenzylamine, 4-methylaminophenethylamine, 3-methylaminophenethylamine, and 2-methylaminophenethylamine;

[0619] Disubstituted amines such as dimethylamine, diethylamine, methylethylamine, N-methyl-N-(2-hydroxyethyl)amine, N-ethyl-N-(2-hydroxyethyl)amine, and bis(2-hydroxyethyl)amine (diethanolamine).

[0620] Examples of the compound represented by formula (A7-2) include:

[0621] Alkane diols such as ethylene glycol, 1,3-propanediol, and 1,4-butanediol;

[0622] Monoalkyl ethers of alkane diols such as ethylene glycol monomethyl ether, 1,3-propanediol monomethyl ether, and 1,4-butanediol monomethyl ether;

[0623] Aminoalkanols such as 2-aminoethanol, 3-aminopropanol, and 4-aminobutanol;

[0624] Alkylaminoalkanols such as 2-methylaminoethanol, 3-methylaminopropanol, 4-methylaminobutanol, 2-ethylaminoethanol, 3-ethylaminopropanol, and 4-ethylaminobutanol;

[0625] Hydroxyalkylaminoalkanols such as 2-(2-hydroxyethylamino)ethanol, 3-(2-hydroxyethylamino)propanol, and 4-(2-hydroxyethylamino)butanol;

[0626] Disubstituted aminoalkylalkanols such as 2-dimethylaminoethanol, 3-dimethylaminopropanol, 4-dimethylaminobutanol, 2-diethylaminoethanol, 3-diethylaminopropanol, 4-diethylaminobutanol, 2-(N-methyl-N-ethylamino)ethanol, 3-(N-methyl-N-ethylamino)propanol, 4-(N-methyl-N-ethylamino)butanol, 2-(N-methyl-N-2-hydroxyethylamino)ethanol, 3-(N-methyl-N-2-hydroxyethylamino)propanol, 4-(N-methyl-N-2-hydroxyethylamino)butanol, 2-(N-ethyl-N-2-hydroxyethylamino)ethanol, 3-(N-ethyl-N-2-hydroxyethylamino)propanol, 4-(N-ethyl-N-2-hydroxyethylamino)butanol, 2-[bis(2-hydroxyethyl)amino]ethanol, 3-[bis(2-hydroxyethyl)amino]propanol, and 4-[bis(2-hydroxyethyl)amino]butanol;

[0627] Dihydroxyarenes such as 4-hydroxyphenol (hydroquinone), 3-hydroxyphenol (resorcinol), and 2-hydroxyphenol (catechol);

[0628] Alkoxyphenols such as 4-methoxyphenol, 3-methoxyphenol, and 2-methoxyphenol;

[0629] Alkylaminophenols such as 4-methylaminophenol, 3-methylaminophenol, and 2-methylaminophenol;

[0630] Hydroxyarylalkanols such as 4-hydroxybenzyl alcohol, 3-hydroxybenzyl alcohol, 2-hydroxybenzyl alcohol, 4-hydroxyphenethyl alcohol, 3-hydroxyphenethyl alcohol, and 2-hydroxyphenethyl alcohol;

[0631] Alkoxyarylalkanols such as 4-methoxybenzyl alcohol, 3-methoxybenzyl alcohol, 2-methoxybenzyl alcohol, 4-methoxyphenethyl alcohol, 3-methoxyphenethyl alcohol, and 2-methoxyphenethyl alcohol;

[0632] Aminoarylalkanols such as 4-aminobenzyl alcohol, 3-aminobenzyl alcohol, 2-aminobenzyl alcohol, 4-aminophenethyl alcohol, 3-aminophenethyl alcohol, and 2-aminophenethyl alcohol;

[0633] Methylaminoarylalkanols such as 4-methylaminobenzyl alcohol, 3-methylaminobenzyl alcohol, 2-methylaminobenzyl alcohol, 4-methylaminophenethyl alcohol, 3-methylaminophenethyl alcohol, and 2-methylaminophenethyl alcohol; and so on.

[0634] Examples of the compound represented by formula (A7-3) include:

[0635] Mercaptoalkanols such as 2-mercaptoethanol, 3-mercaptopropanol, and 4-mercaptobutanol;

[0636] Alkyl ethers of mercaptoalkanols such as 1-mercapto-2-methoxyethane, 1-mercapto-3-methoxypropane, and 1-mercapto-4-methoxybutane;

[0637] Mercaptoalkylamines such as 1-mercapto-2-aminoethane, 1-mercapto-3-aminopropane, and 1-mercapto-4-aminobutane;

[0638] N-(alkylmercapto)alkylamines such as 1-mercapto-2-methylaminoethane, 1-mercapto-3-methylaminopropane, 1-mercapto-4-methylaminobutane, 1-mercapto-2-ethylaminoethane, 1-mercapto-3-ethylaminopropane, and 1-mercapto-4-ethylaminobutane;

[0639] Mercapto(hydroxyalkylamino)alkanes such as 1-mercapto-2-(2-hydroxyethylamino)ethane, 1-mercapto-3-(2-hydroxyethylamino)propane, and 1-mercapto-4-(2-hydroxyethylamino)butane;

[0640] N-(alkyl mercapto)-N,N-disubstituted-alkylamines such as 1-mercapto-2-dimethylaminoethane, 1-mercapto-3-dimethylaminopropane, 1-mercapto-4-dimethylaminobutane, 1-mercapto-2-diethylaminoethane, 1-mercapto-3-diethylaminopropane, 1-mercapto-4-diethylaminobutane, 1-mercapto-2-(N-methyl-N-ethylamino)ethane, 1-mercapto-3-(N-methyl-N-ethylamino)propane, 1-mercapto-4-(N-methyl-N-ethylamino)butane, 1-mercapto-2-(N-methyl-N-2-hydroxyethylamino)ethane, 1-mercapto-3-(N-methyl-N-2-hydroxyethylamino)propane, 1-mercapto-4-(N-methyl-N-2-hydroxyethylamino)butane, 1-mercapto-2-(N-ethyl-N-2-hydroxyethylamino)ethane, 1-mercapto-3-(N-ethyl-N-2-hydroxyethylamino)propane, 1-mercapto-4-(N-ethyl-N-2-hydroxyethylamino)butane, 1-mercapto-2-[bis(2-hydroxyethyl)amino]ethane, 1-mercapto-3-[bis(2-hydroxyethyl)amino]propane, and 1-mercapto-4-[bis(2-hydroxyethyl)amino]butane;

[0641] Mercapto-substituted hydroxyarenes such as 4-mercaptophenol, 3-mercaptophenol, and 2-mercaptophenol;

[0642] Alkoxy thiophenols such as 4-methoxy thiophenol, 3-methoxy thiophenol, and 2-methoxy thiophenol;

[0643] Alkylamino thiophenols such as 4-methylamino thiophenol, 3-methylamino thiophenol, and 2-methylamino thiophenol;

[0644] Hydroxyarylalkylthiols such as 4-hydroxybenzyl mercaptan, 3-hydroxybenzyl mercaptan, 2-hydroxybenzyl mercaptan, 4-hydroxyphenethyl mercaptan, 3-hydroxyphenethyl mercaptan, and 2-hydroxyphenethyl mercaptan;

[0645] Alkoxyarylalkylthiols such as 4-methoxybenzyl mercaptan, 3-methoxybenzyl mercaptan, 2-methoxybenzyl mercaptan, 4-methoxyphenethyl mercaptan, 3-methoxyphenethyl mercaptan, and 2-methoxyphenethyl mercaptan;

[0646] Aminoarylalkylthiols such as 4-aminobenzyl mercaptan, 3-aminobenzyl mercaptan, 2-aminobenzyl mercaptan, 4-aminophenethyl mercaptan, 3-aminophenethyl mercaptan, and 2-aminophenethyl mercaptan;

[0647] Methylaminoarylalkylthiols such as 4-methylaminobenzyl mercaptan, 3-methylaminobenzyl mercaptan, 2-methylaminobenzyl mercaptan, 4-methylaminophenethyl mercaptan, 3-methylaminophenethyl mercaptan, and 2-methylaminophenethyl mercaptan; and so on.

[0648] The method of condensing a dihalotriazine compound represented by inclusive formula (A3) and optionally a dihalotriazine compound represented by formula (A6) with an aromatic diamine compound represented by formula (A5-1), an aromatic diol represented by formula (A5-2), or an aromatic dithiol represented by formula (A5-3) is the same as the method described for the first embodiment.

[0649] By allowing a compound represented by any one of formulas (A7-1) to (A7-3) to be present in the above condensation reaction, the group represented by the aforementioned formula (1-1) is generated at the end of the molecular chain of the resulting polymer (2A).

[0650] In this case, the compound represented by any one of formulas (A7-1) to (A7-3) can be added to the reaction system at the start of the condensation reaction or can be added to the reaction system during the course of the condensation reaction.

[0651] Alternatively, the polymer formed by the above condensation reaction can be reacted with a compound represented by any one of formulas (A7-1) to (A7-3), thereby introducing the group represented by the aforementioned formula (1-1) into the end of the molecular chain of the polymer.

[0652] The reaction conditions in this case can be the same as those for condensing a dihalotriazine compound with an aromatic diamine compound represented by formula (A5-1), an aromatic diol represented by formula (A5-2), or an aromatic dithiol represented by formula (A5-3).

[0653] The organic solvent used in the condensation reaction is the same as the organic solvent used in the condensation reaction described for the first embodiment.

[0654] The amount of the organic solvent used is the same as the amount of the organic solvent used in the condensation reaction described for the first embodiment.

[0655] Regarding the amount of the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol represented by formula (A5-3) used in the production of polymer (2A), per 1 mole of the dihalotriazine compound containing the dihalotriazine compound represented by formula (A3) and optionally the dihalotriazine compound represented by formula (A6), it is preferably 0.8 mole or more and 2.0 moles or less, more preferably 0.9 mole or more and 1.8 moles or less, still more preferably 0.95 mole or more and 1.6 moles or less, and particularly preferably 1.0 mole or more and 1.5 moles or less.

[0656] The amount of the compound represented by any one of formulas (A7-1) to (A7-3) used is not particularly limited as long as the desired effect is not impaired.

[0657] With respect to 1 mole of the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), or the aromatic dithiol represented by formula (A5-3), the amount of the compound represented by any one of formulas (A7-1) to (A7-3) used is preferably 0.1 mole or more and 2 moles or less, more preferably 0.2 mole or more and 1.8 moles or less, and still more preferably 0.5 mole or more and 1.5 moles or less.

[0658] By using the compound represented by any one of formulas (A7-1) to (A7-3) in the above-mentioned range, a sufficient amount of the group represented by formula (A1-1) can be introduced into the ends of the polymer (2A), and an increase in molecular weight during storage can be suppressed.

[0659] When producing the polymer (2A) by polymerization, the reaction temperature is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower.

[0660] When closing the ends of the polymer (2A), the reaction temperature is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower, and still more preferably 20°C or higher and 60°C or lower.

[0661] When producing the polymer (2A) by polymerization, the reaction temperature is preferably higher than the reaction temperature when closing the ends of the polymer (2A).

[0662] The reaction time when producing the polymer (2A) by polymerization and when closing the ends of the polymer is not particularly limited. For example, when producing the polymer (2A) by polymerization, the reaction time is preferably 5 minutes or more and 48 hours or less, more preferably 10 minutes or more and 40 hours or less, and still more preferably 30 minutes or more and 30 hours or less.

[0663] When closing the ends of the polymer (2A), the reaction time is preferably 5 minutes or more and 12 hours or less, more preferably 10 minutes or more and 6 hours or less, and still more preferably 30 minutes or more and 3 hours or less.

[0664] The reaction time when polymerizing to obtain the polymer (2A) is preferably longer than the reaction time when closing the ends of the polymer (2A).

[0665] <Non-photosensitive liquid composition>

[0666] The non-photosensitive liquid composition contains the aforementioned polymer (2A) containing a structural unit represented by formula (A1). The non-photosensitive liquid composition is the same as the non-photosensitive liquid composition described for the first embodiment except that the polymer (1A) is changed to the polymer (2A).

[0667] The non-photosensitive liquid composition contains the aforementioned polymer (2A) and an organic solvent (S).

[0668] In the case where the aforementioned polymer (2A) has a hydroxyl group protected with an acetal protecting group as R a1 or in the case where R a1 is a carboxyl group protected with an acid dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0669] The non-photosensitive liquid composition preferably contains a crosslinkable compound (B).

[0670] The crosslinkable compound (B) and the thermal acid generator (C) are the same as the crosslinkable compound (B) and the thermal acid generator (C) described for the first embodiment.

[0671] The usage amount of the crosslinkable compound (B) and the usage amount of the thermal acid generator (C) are the same as the usage amount of the crosslinkable compound (B) and the usage amount of the thermal acid generator (C) described for the first embodiment.

[0672] 〔Surfactant (D)〕

[0673] The non-photosensitive liquid composition may further contain a surfactant (surface conditioner) in order to improve film-forming properties, coatability, defoaming properties, leveling properties, etc. The specific examples and usage amounts of the surfactant (D) are the same as the specific examples and usage amounts of the surfactant (D) described for the first embodiment.

[0674] 〔Other components〕

[0675] The non-photosensitive liquid composition may contain additives such as a defoaming agent, a silane coupling agent, a coloring agent (pigment, dye), and a crosslinking agent as needed. Any additive may use a conventionally known compound.

[0676] 〔Manufacturing method of non-photosensitive liquid composition〕

[0677] The non-photosensitive liquid composition can be manufactured by the following method: After mixing optional components as needed into the essential components described above, each component is uniformly dissolved in the organic solvent (S). The non-photosensitive liquid composition may also be filtered using a filter with a desired mesh as needed.

[0678] <Manufacturing method of molded body>

[0679] A molded body can be manufactured by a method including the following steps:

[0680] A step of molding the aforementioned non-photosensitive liquid composition; and

[0681] A step of removing an organic solvent (S) from a formed non-photosensitive liquid composition by heating.

[0682] The method for manufacturing the molded body is the same as the method for manufacturing the molded body described for the first embodiment.

[0683] The thus obtained molded body exhibits a high refractive index. Specifically, the refractive index of the molded body, measured with respect to light having a wavelength of 550 nm, is preferably 1.74 or more, more preferably 1.75 or more.

[0684] Such a molded body exhibiting a high refractive index can be suitably used as various optical components. The optical component is preferably a film or a microlens. The optical component formed from the molded body of the non-photosensitive liquid composition can be suitably used in various optical elements. The molded body as a film can be used as a high refractive index film in various optical elements. The molded body as a microlens can be particularly suitably used in optical elements such as CCD and CMOS.

[0685] <<Third Embodiment>>

[0686] <<Polymer (3A) Containing a Triazine Ring>>

[0687] The polymer (3A) containing a triazine ring includes a structural unit represented by the following formula (A1). The polymer may also include other structural units in addition to the structural unit represented by the following formula (A1). As the other structural unit, a structural unit represented by the following formula (A2) is preferred.

[0688] Hereinafter, the polymer (3A) containing a triazine ring will also be referred to as "polymer (3A)".

[0689] The weight average molecular weight of the above-mentioned polymer (3A) is 4,000 or more and 20,000 or less.

[0690] The above-mentioned polymer (3A) exhibits a high refractive index, and even when exposed to light for a long time, the light transmittance is not easily reduced.

[0691] Hereinafter, the structural unit represented by the formula (A1) will also be referred to as "unit (A1)". The structural unit represented by the formula (A2) will also be referred to as "unit (A2)".

[0692] [Chemical formula 42]

[0693]

[0694] In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group. R a1It is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected by an acetal protecting group, or a carboxyl group protected by an acid-dissociable group. The acetal protecting group is -CHR A1 -OR A2 The group represented by R A1 is a hydrogen atom or an alkyl group. A2 is an alkyl group. A1 With R A2 They may be bonded to each other to form a ring. 1 and X 2 Each independently is -NR a2 -, -O- or -S-. R a2 X is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Bonded to Ar 1 The aromatic ring in the group containing an aromatic group. 2 Bonded to Ar 2 The aromatic ring in the group containing an aromatic group.

[0695] [Chemical Formula 43]

[0696]

[0697] In formula (A2), Ar 2 and Ar 3 is a group containing an aromatic group. 1 and X 2 Each independently is -NR a2 -, -O- or -S-. R a2 X is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. 1 Bonded to Ar 3 The aromatic ring in the group containing an aromatic group. 2 Bonded to Ar 2 The aromatic ring in the group containing an aromatic group.

[0698] The polymer (3A) including the unit (A1) has a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid-dissociable group.

[0699] The above-mentioned polymer is soluble in various organic solvents such as nitrogen-containing polar organic solvents and ketone-based solvents.

[0700] However, by deprotecting the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or by deprotecting the carboxyl group protected with an acid dissociable group, the above polymer becomes poorly soluble in organic solvents. The deprotected polymer having a hydroxyl group, an amino group, or a carboxyl group can be crosslinked with a polymerizable monomer capable of reacting with the hydroxyl group, the amino group, or the carboxyl group, thereby becoming even more poorly soluble in organic solvents. As the polymerizable monomer, the crosslinkable compound (B) described later can be mentioned.

[0701] Therefore, the above polymer (3A) is easily processed as a solution. On the other hand, a molded article produced using a solution of the aforementioned polymer under conditions where the tert-butoxycarbonyloxy group, the tert-butoxycarbonylamino group, or the hydroxyl group protected with an acetal protecting group, or the carboxyl group protected with an acid dissociable group is deprotected is poorly soluble in organic solvents.

[0702] The ratio of the mass of the unit (A1) to the mass of the polymer (3A) is not particularly limited within the range that does not impair the desired effect. Regarding the ratio of the mass of the unit (A1) to the mass of the polymer (3A), it can be 10% by mass or more, 20% by mass or more, 30% by mass or more, 50% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 100% by mass relative to the mass of the polymer (3A).

[0703] When the polymer (3A) contains the unit (A1) and the unit (A2), the ratio of the number of moles of the unit (A1) to the total number of moles of the unit (A1) and the unit (A2) is preferably 10 mol% or more and 70 mol% or less, more preferably 20 mol% or more and 70 mol% or less, and particularly preferably 30 mol% or more and 60 mol% or less.

[0704] [Unit (A1)]

[0705] The unit (A1) is the unit represented by the aforementioned formula (A1). The formula (A1) is the same as the formula (A1) described for the first embodiment. That is, the unit (A1) is the same as the unit (A1) possessed by the triazine ring-containing polymer (A1) related to the first embodiment.

[0706] [Unit (A2)]

[0707] As described above, the polymer (3A) may also contain the unit (A2) as other structural units in addition to the unit (A1).

[0708] The unit (A2) is the unit represented by the aforementioned formula (A2). The formula (A2) is the same as the formula (A2) described for the first embodiment. That is, the unit (A2) is the same as the unit (A2) possessed by the triazine ring-containing polymer (A1) related to the first embodiment.

[0709] The above-mentioned polymer (3A) can be obtained by reacting a dihalotriazine compound represented by the following formula (A3) and a dihalotriazine compound represented by the formula (A6) with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0710] In this case, the polymer (3A) is mostly a mixture of molecules having halogen atoms at both ends, molecules having a halogen atom at one end and an amino group, a hydroxyl group, or a mercapto group at the other end, and molecules having an amino group, a hydroxyl group, or a mercapto group at both ends.

[0711] When the polymer (3A) has a halogen terminal derived from a dihalotriazine compound represented by the following formula (A3) or a dihalotriazine compound represented by the formula (A6), it is also preferable to block the halogen terminal with an amine compound having one amino group.

[0712] The method of blocking the halogen terminal with an amine compound having one amino group is as described for the first mode.

[0713] As described above, the weight-average molecular weight of the polymer (3A) is 4,000 or more and 20,000 or less. The weight-average molecular weight of the polymer is preferably 4,200 or more and 18,000 or less, more preferably 4,400 or more and 16,000 or less, further preferably 4,600 or more and 14,000 or less, further more preferably 4,800 or more and 12,000 or less, and particularly preferably 5,000 or more and 10,000 or less.

[0714] The weight-average molecular weight is the molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0715] If the molecular weight of the polymer (3A) is within the above range, the polymer (3A) is easily soluble in various organic solvents, and the polymer (3A) can provide a molded article with excellent light resistance.

[0716] 〔Method for producing polymer (3A)〕

[0717] The method for producing the polymer (3A) described above is not particularly limited, as long as it is a method for producing a polymer containing the unit (A1) and having a weight-average molecular weight of 4,000 or more and 20,000 or less.

[0718] Typically, the above polymer is produced by condensing a dihalotriazine compound with an aromatic diamine compound represented by the following formula (A5-1), an aromatic diol represented by the following formula (A5-2), or an aromatic dithiol represented by the following formula (A5-3).

[0719] In the above method, the condensation of the dihalotriazine compound with the aromatic diamine compound represented by the following formula (A5-1), the aromatic diol represented by the following formula (A5-2), or the aromatic dithiol represented by the following formula (A5-3) is carried out until a polymer having a desired weight average molecular weight is formed.

[0720] The dihalotriazine compound used for producing the polymer contains a compound represented by the following formula (A3). The compound represented by the formula (A3) can supply the unit (A1) by condensation with a compound represented by any one of the formulas (A5-1) to (A5-3).

[0721] The dihalotriazine compound represented by the formula (A3) is the same as the dihalotriazine compound represented by the formula (A3) described in the first embodiment.

[0722] When the polymer contains the unit (A2), the dihalotriazine compound contains a dihalotriazine compound represented by the following formula (A6). The compound represented by the formula (A6) is included. The dihalotriazine compound represented by the formula (A6) can supply the unit (A2) by condensation with a compound represented by any one of the formulas (A5-1) to (A5-3).

[0723] The dihalotriazine compound represented by the formula (A6) is the same as the dihalotriazine compound represented by the formula (A6) described in the first embodiment.

[0724] [Chemical formula 44]

[0725]

[0726] In the formula (A3), Hal is a halogen atom. Ar 1 is a group containing an aromatic group. R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group. The acetal protecting group is -CHR A1 -O-R A2 represents a group. R A1 is a hydrogen atom or an alkyl group. R A2 is an alkyl group. R A1 and R A2 may be bonded to each other to form a ring. X 1 are each independently -NRa2 -、 -O- or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 1 .

[0727] [Chemical Formula 45]

[0728]

[0729] In formula (A6), Hal is a halogen atom. Ar 3 is a group containing an aromatic group. X 1 are each independently -NR a2 -, -O- or -S-. R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 3 .

[0730] Ar 2 -(NR a2 H)2 ··· (A5-1)

[0731] Ar 2 -(OH)2 ··· (A5-2)

[0732] Ar 2 -(SH)2 ··· (A5-3)

[0733] The aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), and the aromatic dithiol represented by formula (A5-3) are the same as the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2), and the aromatic dithiol represented by formula (A5-3) described in the first embodiment.

[0734] The method for condensing a dihalotriazine compound containing a dihalotriazine compound represented by formula (A3) and optionally a dihalotriazine compound represented by formula (A6) with an aromatic diamine compound represented by formula (A5-1), an aromatic diol represented by formula (A5-2), or an aromatic dithiol represented by formula (A5-3) is not particularly limited as long as a polymer (3A) having a desired weight average molecular weight can be obtained.

[0735] Typically, the dihalotriazine compound represented by inclusive formula (A3) and optionally the dihalotriazine compound represented by formula (A6), and the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2) or the aromatic dithiol represented by formula (A5-3) are mixed in an organic solvent to produce the aforementioned polymer (3A).

[0736] The organic solvent used in the condensation reaction is the same as the organic solvent used in the condensation reaction described for the first embodiment.

[0737] The amount of the organic solvent used is the same as the amount of the organic solvent used in the first embodiment.

[0738] Regarding the amount of the aromatic diamine compound represented by formula (A5-1), the aromatic diol represented by formula (A5-2) or the aromatic dithiol represented by formula (A5-3) used in producing the polymer, relative to 1 mole of the dihalotriazine compound containing the dihalotriazine compound represented by formula (A3), it is preferably 0.8 mole or more and 1.2 moles or less, more preferably 0.9 mole or more and 1.1 moles or less, and still more preferably 0.95 mole or more and 1.05 moles or less.

[0739] When producing the polymer (3A), the ends of the polymer (3A) may or may not be end-capped, but end-capping is preferred.

[0740] When producing the polymer (3A) by polymerization, the reaction temperature is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower, still more preferably 40°C or higher and 100°C or lower, and particularly preferably 50°C or higher and 80°C or lower.

[0741] When end-capping the ends of the polymer (3A), the reaction temperature is, for example, preferably 0°C or higher and 200°C or lower, more preferably 20°C or higher and 150°C or lower, and still more preferably 20°C or higher and 60°C or lower.

[0742] The reaction temperature for producing the polymer (3A) by polymerization is preferably higher than the reaction temperature for end-capping the ends of the polymer (3A).

[0743] The reaction time is not particularly limited. For example, when producing the polymer (3A) by polymerization, the reaction time is preferably 5 minutes or more and 120 hours (5 days) or less, more preferably 30 minutes or more and 96 hours (4 days) or less, still more preferably 60 minutes or more and 72 hours (3 days) or less, even more preferably 120 minutes or more and 48 hours or less, and particularly preferably 240 minutes or more and 36 hours or less.

[0744] When capping the ends of the polymer (3A), the reaction time is preferably 5 minutes or more and 12 hours or less, more preferably 10 minutes or more and 6 hours or less, and still more preferably 30 minutes or more and 3 hours or less.

[0745] When producing the polymer (3A) by polymerization, the reaction time is preferably longer than the reaction time for capping the ends of the polymer (3A).

[0746] From the viewpoint of easily obtaining a polymer (3A) having a weight average molecular weight of 4,000 or more and 20,000 or less, the condensation reaction is preferably carried out at 40°C or more and 100°C or less for 120 minutes or more and 48 hours or less.

[0747] From the viewpoint of easily obtaining a polymer having a weight average molecular weight of 4,000 or more and 20,000 or less, the total concentration of the dihalotriazine compound and the compound represented by any one of the formulas (A5-1) to (A5-3) in the reaction solution when starting the condensation of the dihalotriazine compound and the compound represented by any one of the formulas (A5-1) to (A5-3) is preferably 120 mmol / L or more, more preferably 120 mmol / L or more and 600 mmol / L or less, and still more preferably 180 mmol / L or more and 360 mmol / L or less.

[0748] <Non-photosensitive liquid composition>

[0749] The non-photosensitive liquid composition contains the aforementioned polymer (3A) containing a structural unit represented by the formula (A1). The non-photosensitive liquid composition is the same as the non-photosensitive liquid composition described for the first embodiment except that the polymer (1A) is changed to the polymer (3A).

[0750] The non-photosensitive liquid composition contains the aforementioned polymer (3A) and an organic solvent (S).

[0751] When the aforementioned polymer (3A) has a hydroxyl group protected by an acetal protecting group as R a1 or when R a1 is a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

[0752] The non-photosensitive liquid composition preferably contains a crosslinkable compound (B).

[0753] The crosslinkable compound (B) and the thermal acid generator (C) are the same as the crosslinkable compound (B) and the thermal acid generator (C) described for the first embodiment.

[0754] The usage amount of the crosslinkable compound (B) and the usage amount of the thermal acid generator (C) are the same as those of the crosslinkable compound (B) and the thermal acid generator (C) described for the first embodiment.

[0755] [Surfactant (D)]

[0756] The non-photosensitive liquid composition may further contain a surfactant (surface conditioner) in order to improve film forming properties, coating properties, defoaming properties, leveling properties, etc. The specific examples and usage amounts of the surfactant (D) are the same as those of the surfactant (D) described for the first embodiment.

[0757] [Other components]

[0758] The non-photosensitive liquid composition may contain additives such as an antifoaming agent, a silane coupling agent, a colorant (pigment, dye), a crosslinking agent, etc. as needed. Any additive may use a conventionally known compound.

[0759] [Manufacturing method of non-photosensitive liquid composition]

[0760] The non-photosensitive liquid composition can be manufactured by the following method: After mixing optional components as needed into the essential components described above, dissolve each component uniformly in the organic solvent (S). The non-photosensitive liquid composition may also be filtered using a filter with a desired mesh as needed.

[0761] [Manufacturing method of molded body]

[0762] A method including the following steps can be used to manufacture a molded body:

[0763] A step of molding the aforementioned non-photosensitive liquid composition; and

[0764] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0765] The manufacturing method of the molded body is the same as that of the molded body described for the first embodiment.

[0766] The molded body obtained in this way exhibits a high refractive index. Specifically, the refractive index of the molded body, measured by the refractive index of light with a wavelength of 550 nm, is preferably 1.74 or more, more preferably 1.75 or more.

[0767] Such a molded article showing a high refractive index can be suitably used as various optical components. The optical component is preferably a film or a microlens. The optical component formed from the molded article of the non-photosensitive liquid composition can be suitably used in various optical elements. The molded article as a film can be used as a high refractive index film in various optical elements. The molded article as a microlens can be particularly suitably used in optical elements such as CCD and CMOS.

[0768] As described above, the inventors of the present application provide the following (1) to (16) for the first embodiment.

[0769] (1) A polymer containing a triazine ring, which comprises a structural unit represented by the following formula (A1) and a structural unit represented by the following formula (A2).

[0770] [Chemical formula 46]

[0771]

[0772] (In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group,

[0773] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group,

[0774] The hydroxyl group protected with an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 represents,

[0775] R A1 is a hydrogen atom or an alkyl group,

[0776] R A2 is an alkyl group,

[0777] R A1 and R A2 may be bonded to each other to form a ring,

[0778] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0779] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0780] X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 1

[0781] X 2 bonded to the aromatic ring in the group containing an aromatic group as Ar 2 (.))

[0782] [Chemical formula 47]

[0783]

[0784] (In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group,

[0785] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0786] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0787] X 1 is bonded to the aromatic ring in the group containing an aromatic group as Ar 3 (,

[0788] X 2 is bonded to the aromatic ring in the group containing an aromatic group as Ar 2 (.)

[0789] (2) The triazine ring-containing polymer according to (1), wherein the ratio of the number of moles of the structural unit represented by formula (A1) to the total number of moles of the structural unit represented by formula (A1) and the structural unit represented by formula (A2) is 10 mol% or more and 70 mol% or less.

[0790] (3) The triazine ring-containing polymer according to (1) or (2), wherein R a1 is tert-butoxycarbonylamino or tert-butoxycarbonyloxy.

[0791] (4) The triazine ring-containing polymer according to any one of (1) to (3), wherein X 2 in formula (A1) and formula (A2) is -NR a2 - or -O-.

[0792] (5) The method for producing the triazine ring-containing polymer according to (1), which includes a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3),

[0793] The dihalotriazine compound includes a compound represented by the following formula (A3) and a compound represented by the following formula (A6).

[0794] Ar 2 -(NR a2 H)2···(A5-1)

[0795] Ar 2 -(OH)2···(A5-2)

[0796] Ar 2 -(SH)2···(A5-3)

[0797] (In formulas (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.)

[0798] [Chemical formula 48]

[0799]

[0800] (In formula (A3), Hal is a halogen atom,

[0801] Ar 1 is a group containing an aromatic group,

[0802] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group,

[0803] The hydroxyl group protected with an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 wherein,

[0804] R A1 is a hydrogen atom or an alkyl group,

[0805] R A2 is an alkyl group,

[0806] R A1 and R A2 may be bonded to each other to form a ring,

[0807] X 1 are each independently -NR a2 -, -O-, or -S-,

[0808] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0809] X 1 is bonded to Ar as 1the aromatic ring in the group containing an aromatic group.)

[0810] [Chemical Formula 49]

[0811]

[0812] (In formula (A6), Hal is a halogen atom,

[0813] Ar 3 is a group containing an aromatic group,

[0814] X 1 each independently is -NR a2 -, -O-, or -S-,

[0815] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0816] X 1 is bonded to the aromatic ring in the group containing an aromatic group as Ar 3 .)

[0817] (6) A non-photosensitive liquid composition, which comprises a polymer (1A) containing a triazine ring and an organic solvent (S),

[0818] The polymer (1A) containing a triazine ring is the polymer containing a triazine ring described in any one of (1) to (4),

[0819] When R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further comprises a thermal acid generator (C).

[0820] (7) The non-photosensitive liquid composition as described in (6), which further comprises a crosslinking compound (B).

[0821] (8) The non-photosensitive liquid composition as described in (7), wherein the crosslinking compound (B) is an aromatic compound (Bi) containing two or more crosslinking groups, a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinking groups, or an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinking groups,

[0822] The sulfur-containing compound (Bii) is a compound that does not belong to the aromatic compound (Bi),

[0823] The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii).

[0824] The aliphatic compound (Biv) is a compound that does not belong to the sulfur-containing compound (Bii) and the isocyanate compound (Biii).

[0825] (9) The non-photosensitive liquid composition according to (8), wherein the crosslinkable group is an epoxy group, a thiirane group, or an isocyanate group.

[0826] (10) The non-photosensitive liquid composition according to any one of (6) to (9), wherein the organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a diol, or a monoalkyl ether of a diol.

[0827] (11) A method for manufacturing a molded article, which includes the following steps:

[0828] A step of molding the non-photosensitive liquid composition according to any one of (6) to (10); and

[0829] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0830] (12) The method for manufacturing a molded article according to (11), wherein the non-photosensitive liquid composition is molded into a film shape by coating the non-photosensitive liquid composition on a substrate.

[0831] (13) A molded article of the non-photosensitive liquid composition according to any one of (6) to (10).

[0832] (14) An optical component formed of the molded article according to (13).

[0833] (15) The optical component according to (14), which is a film or a microlens.

[0834] (16) An optical element including the optical component according to (14).

[0835] In addition, as described above, the inventors of the present application provide the following (1) to (18) for the second embodiment.

[0836] (1) A polymer containing a triazine ring, which includes a structural unit represented by the following formula (A1).

[0837] At least a part of the terminals of the molecular chain of the polymer containing a triazine ring has a group represented by the following formula (A1-1).

[0838] [Chemical formula 50]

[0839]

[0840] (In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group,

[0841] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group,

[0842] The hydroxyl group protected with an acetal protecting group is a group represented by -O-CHR A1 -O-R A2 wherein,

[0843] R A1 is a hydrogen atom or an alkyl group,

[0844] R A2 is an alkyl group,

[0845] R A1 and R A2 may be bonded to each other to form a ring,

[0846] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0847] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0848] X 1 is bonded to the aromatic ring in the group containing an aromatic group as Ar 1 and

[0849] X 2 is bonded to the aromatic ring in the group containing an aromatic group as Ar 2 .)

[0850] -X 2 -X 3 -X 4 ···(A1-1)

[0851] (In formula (A1-1), X 2 is the same as X 2 in formula (A1),

[0852] X 3 is a divalent hydrocarbon group,

[0853] X 4 is -OR a3 or -N(R a3) 2,

[0854] R a3 is a hydrogen atom or an alkyl group which may have a substituent,

[0855] When the hydrocarbon group as X 3 is a group containing an aromatic group, X 4 is not an amino group.)

[0856] (2) The polymer containing a triazine ring as described in (1), wherein R a1 is a tert-butoxycarbonylamino group or a tert-butoxycarbonyloxy group.

[0857] (3) The polymer containing a triazine ring as described in (1) or (2), wherein X 2 is -NR a2 - or -O-.

[0858] (4) The polymer containing a triazine ring as described in any one of (1) to (3), wherein the divalent hydrocarbon group as X 3 is an alkylene group.

[0859] (5) The polymer containing a triazine ring as described in any one of (1) to (4), which comprises a structural unit represented by the following formula (A2).

[0860] [Chemical formula 51]

[0861]

[0862] (In the formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group,

[0863] X 1 and X 2 are each independently -NR a2 -, -O- or -S-,

[0864] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0865] X 1 is bonded to an aromatic ring in the group containing an aromatic group as Ar 3 ,

[0866] X 2 is bonded to an aromatic ring in the group containing an aromatic group as Ar 2 .)

[0867] (6) A method for producing a triazine ring-containing polymer according to (1), comprising the step of condensing a dihalogenated triazine compound with a compound represented by any one of the following formulae (A5-1) to (A5-3),

[0868] The dihalogenated triazine compound includes a compound represented by the following formula (A3),

[0869] Condensation of a dihalogenated triazine compound and a compound represented by any one of the formulae (A5-1) to (A5-3) in the presence of a compound represented by any one of the following formulae (A7-1) to (A7-3), or

[0870] A condensation product of a dihalogenotriazine compound and a compound represented by any one of formulae (A5-1) to (A5-3) and a compound represented by any one of formulae (A7-1) to (A7-3) are reacted.

[0871] Ar 2 -(NR a2 H)2···(A5-1)

[0872] Ar 2 -(OH)2···(A5-2)

[0873] Ar 2 -(SH)2···(A5-3)

[0874] (In formula (A5-1) to formula (A5-3), Ar 2 is a group containing an aromatic group, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.

[0875] [Chemical Formula 52]

[0876]

[0877] (In formula (A3), Hal is a halogen atom,

[0878] Ar 1 is a group containing an aromatic group,

[0879] R a1 is a tert-butoxycarbonyloxy group, a tert-butoxycarbonylamino group, or a hydroxyl group protected by an acetal protecting group, or is a carboxyl group protected by an acid-dissociable group,

[0880] The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -OR A2 The group represented by

[0881] R A1is a hydrogen atom or an alkyl group,

[0882] R A2 is an alkyl group,

[0883] R A1 and R A2 may be bonded to each other to form a ring,

[0884] X 1 are each independently -NR a2 -, -O-, or -S-,

[0885] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0886] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 1 .)

[0887] X 4 -X 3 -NR a2 H···(A7-1)

[0888] X 4 -X 3 -OH···(A7-2)

[0889] X 4 -X 3 -SH···(A7-3)

[0890] (In formulas (A7-1) to (A7-3), X 3 and X 4 are the same as X 3 and X 4 in formula (A1-1), and

[0891] R a2 is the same as R a2 in formula (1).)

[0892] (7) The production method according to (6), wherein the dihalotriazine compound contains a compound represented by the following formula (A6).

[0893] [Chemical formula 53]

[0894]

[0895] (In formula (A6), Hal is a halogen atom,

[0896] Ar 3 is a group containing an aromatic group,

[0897] X1 Each independently represents -NR a2 -, -O- or -S-,

[0898] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0899] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 3 ().

[0900] (8) A non-photosensitive liquid composition comprising a polymer (2A) containing a triazine ring and an organic solvent (S),

[0901] The polymer (2A) containing a triazine ring is the polymer containing a triazine ring according to any one of (1) to (5),

[0902] In the case where R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further comprises a thermal acid generator (C).

[0903] (9) The non-photosensitive liquid composition according to (8), further comprising a crosslinkable compound (B).

[0904] (10) The non-photosensitive liquid composition according to (9), wherein the crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups, a triazine ring, a fluorene ring which may have a substituent or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinkable groups,

[0905] The sulfur-containing compound (Bii) is a compound that does not belong to the aromatic compound (Bi),

[0906] The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii),

[0907] The aliphatic compound (Biv) is a compound that does not belong to the sulfur-containing compound (Bii) and the isocyanate compound (Biii).

[0908] (11) The non-photosensitive liquid composition according to (10), wherein the crosslinkable group is an epoxy group, a thiirane group or an isocyanate group.

[0909] (12) The non-photosensitive liquid composition according to any one of (8) to (11), wherein the organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a diol, or a monoalkyl ether of a diol.

[0910] (13) A method for manufacturing a molded article, comprising the following steps:

[0911] A step of molding the non-photosensitive liquid composition according to any one of (8) to (12); and

[0912] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0913] (14) The method for manufacturing a molded article according to (13), wherein the non-photosensitive liquid composition is molded into a film shape by coating the non-photosensitive liquid composition on a substrate.

[0914] (15) A molded article of the non-photosensitive liquid composition according to any one of (8) to (12).

[0915] (16) An optical component formed of the molded article according to (15).

[0916] (17) The optical component according to (16), which is a film or a microlens.

[0917] (18) An optical element including the optical component according to (16).

[0918] In addition, as described above, the inventors of the present application provide the following (1) to (19) for the third embodiment.

[0919] (1) A polymer containing a triazine ring, which includes a structural unit represented by the following formula (A1),

[0920] The weight average molecular weight of the polymer containing a triazine ring is 4,000 or more and 20,000 or less.

[0921] [Chemical formula 54]

[0922]

[0923] (In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group,

[0924] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected by an acetal protecting group, or a carboxyl group protected by an acid dissociable group,

[0925] The hydroxyl group protected with an acetal protecting group is -O-CHR A1 -O-R A2 a group represented by

[0926] R A1 is a hydrogen atom or an alkyl group,

[0927] R A2 is an alkyl group,

[0928] R A1 and R A2 can be bonded to each other to form a ring,

[0929] X 1 and X 2 are each independently -NR a2 -, -O-, or -S-,

[0930] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0931] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 1 and X<(

[0932] is bonded to an aromatic ring in a group containing an aromatic group as Ar 2 and X 2 (.)

[0933] (2) The triazine ring-containing polymer according to (1), wherein R a1 is tert-butoxycarbonylamino or tert-butoxycarbonyloxy.

[0934] (3) The triazine ring-containing polymer according to (1) or (2), wherein X 2 is -NR a2 - or -O-.

[0935] (4) The triazine ring-containing polymer according to any one of (1) to (3), which comprises a structural unit represented by the following formula (A2).

[0936] [Chemical formula 55]

[0937]

[0938] (In the formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group,

[0939] X 1 and X 2 are each independently -NR a2-, -O-, or -S-,

[0940] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0941] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 3 .)

[0942] X 2 is bonded to an aromatic ring in a group containing an aromatic group as Ar 2 .)

[0943] (5) The method for producing a polymer containing a triazine ring according to (1), which includes a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3),

[0944] The dihalotriazine compound includes a compound represented by the following formula (A3).

[0945] Ar 2 -(NR a2 H)2···(A5-1)

[0946] Ar 2 -(OH)2···(A5-2)

[0947] Ar 2 -(SH)2···(A5-3)

[0948] (In formulas (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.)

[0949] [Chemical formula 56]

[0950]

[0951] (In formula (A3), Hal is a halogen atom,

[0952] Ar 1 is a group containing an aromatic group,

[0953] R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or a carboxyl group protected with an acid dissociable group,

[0954] The hydroxyl group protected with an acetal protecting group is -O-CHR A1-O-R A2 The group represented by

[0955] R A1 is a hydrogen atom or an alkyl group,

[0956] R A2 is an alkyl group,

[0957] R A1 and R A2 may be bonded to each other to form a ring,

[0958] X 1 each independently represents -NR a2 -, -O- or -S-,

[0959] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0960] X 1 is bonded to the aromatic ring in the group containing an aromatic group as Ar 1 ).

[0961] (6) The production method according to (5), wherein the condensation of the dihalotriazine compound with the compound represented by any one of formulas (A5-1) to (A5-3) is carried out under the conditions of 40 °C or higher and 100 °C or lower, and 120 minutes or longer and 48 hours or shorter.

[0962] (7) The production method according to (5) or (6), wherein the total concentration of the dihalotriazine compound and the compound represented by any one of formulas (A5-1) to (A5-3) in the reaction solution at the start of the condensation of the dihalotriazine compound with the compound represented by any one of formulas (A5-1) to (A5-3) is 120 mmol / L or higher.

[0963] (8) The production method according to any one of (5) to (7), wherein the dihalotriazine compound contains the compound represented by the following formula (A6).

[0964] [Chemical formula 57]

[0965]

[0966] (In formula (A6), Hal is a halogen atom,

[0967] Ar 3 is a group containing an aromatic group,

[0968] X 1 each independently represents -NR a2 -, -O- or -S-,

[0969] R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent,

[0970] X 1 is bonded to an aromatic ring in a group containing an aromatic group as Ar 3 (.))

[0971] (9) A non-photosensitive liquid composition comprising a polymer (3A) containing a triazine ring and an organic solvent (S),

[0972] The polymer (3A) containing a triazine ring is the polymer containing a triazine ring according to any one of (1) to (4),

[0973] In the case where R a1 is a hydroxyl group protected by an acetal protecting group or a carboxyl group protected by an acid dissociable group, the non-photosensitive liquid composition further comprises a thermal acid generator (C).

[0974] (10) The non-photosensitive liquid composition according to (9), further comprising a crosslinkable compound (B).

[0975] (11) The non-photosensitive liquid composition according to (10), wherein the crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups, a triazine ring, a fluorene ring which may have a substituent, or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinkable groups,

[0976] The sulfur-containing compound (Bii) is a compound that does not belong to the aromatic compound (Bi),

[0977] The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii),

[0978] The aliphatic compound (Biv) is a compound that does not belong to the sulfur-containing compound (Bii) and the isocyanate compound (Biii).

[0979] (12) The non-photosensitive liquid composition according to (11), wherein the crosslinkable group is an epoxy group, a thiirane group, or an isocyanate group.

[0980] (13) The non-photosensitive liquid composition according to any one of (9) to (12), wherein the organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a diol, or a monoalkyl ether of a diol.

[0981] (14) Method for manufacturing a molded body, comprising the following steps:

[0982] A step of molding the non-photosensitive liquid composition according to any one of (9) to (12); and

[0983] A step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

[0984] (15) The method for manufacturing a molded body according to (14), wherein the non-photosensitive liquid composition is molded into a film shape by coating the non-photosensitive liquid composition on a substrate.

[0985] (16) A molded body of the non-photosensitive liquid composition according to (9).

[0986] (17) An optical component formed from the molded body according to (16).

[0987] (18) The optical component according to (17), which is a film or a microlens.

[0988] (19) An optical element comprising the optical component according to (17).

[0989] Examples

[0990] Hereinafter, the present invention will be described in more detail using examples and comparative examples. The present invention is not limited to these examples.

[0991] Hereinafter, examples and comparative examples related to the first embodiment will be described.

[0992] 〔Example 1-1〕

[0993] Cyanuric chloride (3.69 g, 20 mmol) dissolved in 30 mL of THF was added to a 200 mL three-necked flask, and the liquid in the flask was cooled to 0 °C using an ice bath. Then, while stirring the liquid in the flask, 3-tert-butoxycarbonylaminophenylamine (4.17 g, 20 mmol) dissolved in 90 mL of THF was added dropwise to the flask.

[0994] After the dropwise addition, the reaction solution in the flask was stirred for 2 hours. An aqueous potassium carbonate solution (obtained by dissolving potassium carbonate (1.66 g, 12 mmol) in 30 mL of pure water) was added to the reaction solution, and the mixture was stirred at room temperature for 20 minutes. After the reaction mixture and 150 mL of ethyl acetate were placed in a separatory funnel, the aqueous phase was removed by liquid separation. THF and ethyl acetate were removed from the recovered organic phase to obtain a solid residue.

[0995] The residue obtained was purified by silica gel chromatography to obtain a dichlorotriazine compound having the following structure, namely 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine.

[0996] [Chemical formula 58]

[0997]

[0998] m-Phenylenediamine (1.56 g, 14.4 mmol) was placed in a 200 mL three-necked flask. 60 mL of N,N-dimethylacetamide (DMAc) was added to the three-necked flask to dissolve m-phenylenediamine in DMAc. After heating the solution in the three-necked flask to 70 °C, 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine (2.06 g, 5.76 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (2.30 g, 8.64 mmol), which had been dissolved in 60 mL of DMAc, were added to the three-necked flask to initiate a polymerization reaction.

[0999] After continuing the polymerization at 70 °C for 24 hours, the reaction solution was cooled to room temperature. Propylamine (5.92 mL, 72.0 mmol) was added to the cooled reaction solution, and the reaction solution was stirred at room temperature for 1 hour.

[1000] Then, a liquid prepared by mixing 4 mL of an aqueous ammonia solution with a concentration of 28% by mass, 300 mL of water, and 100 mL of methanol was mixed with the reaction solution to precipitate the resulting polymer 1A-1. After recovering the precipitate by filtration, the precipitate was washed with 400 mL of water and 20 mL of hexane. Then, the washed precipitate was dried at 100 °C for 24 hours using a vacuum dryer to obtain 4.62 g of polymer 1A-1. The weight-average molecular weight (Mw, polystyrene conversion) of the obtained polymer 1A-1 measured by GPC was 6,000. The following shows two types of units constituting polymer 1A-1.

[1001] [Chemical formula 59]

[1002]

[1003] [Example 1-2]

[1004] Into a 200 mL three-necked flask, bis-4-aminophenyl sulfide (1.56 g, 7.2 mmol) and m-phenylenediamine (0.78 g, 7.2 mmol) were charged. 60 mL of DMAc was added to the three-necked flask to dissolve bis-4-aminophenyl sulfide and m-phenylenediamine in DMAc. After heating the solution in the three-necked flask to 60 °C, 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine (2.57 g, 7.2 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (1.92 g, 7.2 mmol), which had been dissolved in 60 mL of DMAc, were added to the three-necked flask to initiate a polymerization reaction.

[1005] 2,4-Dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine was obtained by the same method as in Example 1-1.

[1006] After continuing the polymerization at 60 °C for 6 hours, the reaction solution was cooled to room temperature. Propylamine (5.92 mL, 72.0 mmol) was added to the cooled reaction solution, and the reaction solution was stirred at room temperature for 1 hour.

[1007] Then, a liquid prepared by mixing 4 mL of an aqueous ammonia solution with a concentration of 28% by mass, 300 mL of water, and 100 mL of methanol was mixed with the reaction solution to precipitate the resulting polymer 1A-2. After recovering the precipitate by filtration, the precipitate was washed with 400 mL of water and 20 mL of hexane. Then, the washed precipitate was dried at 100 °C for 24 hours using a vacuum dryer to obtain 5.40 g of polymer 1A-2. The weight-average molecular weight (Mw, polystyrene conversion) of the obtained polymer 1A-2 measured by GPC was 4,500. The following shows the four units constituting polymer 1A-2. [[ID=!0]]

[1008] [Chemical formula 60]

[1009]

[1010] [Example 1-3]

[1011] Into a 200 mL three-necked flask, bis-4-aminophenyl sulfide (3.12 g, 14.4 mmol) was charged. 60 mL of DMAc was added to the three-necked flask to dissolve bis-4-aminophenyl sulfide in DMAc. After heating the solution in the three-necked flask to 60 °C, 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine (2.57 g, 7.2 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (1.92 g, 7.2 mmol), which had been dissolved in 60 mL of DMAc, were added to the three-necked flask to initiate a polymerization reaction.

[1012] 2,4-Dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine was obtained by the same method as in Example 1-1.

[1013] After continuing the polymerization at 60 °C for 6 hours, the reaction solution was cooled to room temperature. Propylamine (5.92 mL, 72.0 mmol) was added to the cooled reaction solution, and the reaction solution was stirred at room temperature for 1 hour.

[1014] Then, a liquid prepared by mixing 4 mL of 28 mass% aqueous ammonia solution, 300 mL of water, and 100 mL of methanol was mixed with the reaction solution to precipitate the resulting polymer 1A-3. After recovering the precipitate by filtration, the precipitate was washed with 400 mL of water and 20 mL of hexane. Then, the washed precipitate was dried at 100 °C for 24 hours using a vacuum dryer to obtain 6.10 g of polymer 1A-3. The weight-average molecular weight (Mw, polystyrene equivalent) of the obtained polymer A-3 measured by GPC was 7,800. The following shows two types of units constituting polymer 1A-3.

[1015] [Chemical formula 61]

[1016]

[1017] [Example 1-4]

[1018] 2,4-Dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine was changed to 2,4-dichloro-6-(3-cyanophenyl)amino-1,3,5-triazine, and otherwise, the same operations as in Example 1-3 were carried out to obtain 6.3 g of polymer A-4.

[1019] The weight-average molecular weight (Mw, polystyrene equivalent) of the obtained polymer 1A-4 measured by GPC was 7,600. The following shows two types of units constituting polymer 1A-4.

[1020] [Chemical formula 62]

[1021]

[1022] [Examples 1 - 5]

[1023] 2,4 - Dichloro - 6 - (4 - cyanophenyl)amino - 1,3,5 - triazine (7.2 mmol) was changed to 2,4 - dichloro - 6 - phenylamino - 1,3,5 - triazine (7.2 mmol). Except for this, the operation was carried out in the same manner as in Examples 1 - 3, and 6.2 g of Polymer 1A - 5 was obtained.

[1024] The weight - average molecular weight (Mw, polystyrene - equivalent) of the obtained Polymer 1A - 5 measured by GPC was 7,800. The following shows two kinds of units constituting Polymer 1A - 5.

[1025] [Chemical formula 63]

[1026]

[1027] [Examples 1 - 6]

[1028] The amount of m - phenylenediamine used in the polymerization reaction was changed to 1.31 g (12.1 mmol), and propylamine (5.92 mL, 72.0 mmol) was changed to aminoethanol (4.31 mL, 72.0 mmol). Except for this, the operation was carried out in the same manner as in Example 1 - 1, and 4.0 g of Polymer A - 6 was obtained.

[1029] The weight - average molecular weight (Mw, polystyrene - equivalent) of the obtained Polymer A - 6 measured by GPC was 4,800. The following shows two kinds of units constituting Polymer A - 6.

[1030] [Chemical formula 64]

[1031]

[1032] [Synthesis Example 1 - 1]

[1033] Bis - 4 - aminophenyl sulfide (3.12 g, 14.4 mmol) was charged into a 200 - mL three - necked flask. 60 mL of DMAc was added to the three - necked flask to dissolve bis - 4 - aminophenyl sulfide in DMAc. After heating the solution in the three - necked flask to 60 °C, 2,4 - dichloro - 6 - (3 - tert - butoxycarbonylaminophenyl)amino - 1,3,5 - triazine (5.14 g, 14.4 mmol) dissolved in 60 mL of DMAc was added to the three - necked flask to initiate the polymerization reaction.

[1034] 2,4 - Dichloro - 6 - (3 - tert - butoxycarbonylaminophenyl)amino - 1,3,5 - triazine was obtained by the same method as in Example 1 - 1.

[1035] After continuing the polymerization at 60 °C for 6 hours, the reaction solution was cooled to room temperature. Propylamine (5.92 mL, 72.0 mmol) was added to the cooled reaction solution, and the reaction solution was stirred at room temperature for 1 hour.

[1036] Then, a liquid prepared by mixing 4 mL of an aqueous ammonia solution with a concentration of 28% by mass, 300 mL of water, and 100 mL of methanol was mixed with the reaction solution to precipitate the resulting polymer 1A-7. After recovering the precipitate by filtration, the precipitate was washed with 400 mL of water and 20 mL of hexane. Then, the washed precipitate was dried at 100 °C for 24 hours using a vacuum dryer to obtain 6.70 g of polymer 1A-7. The weight-average molecular weight (Mw, polystyrene conversion) of the obtained polymer 1A-7 measured by GPC was 7,500. The units constituting polymer 1A-7 are shown below.

[1037] [Chemical formula 65]

[1038]

[1039] [Synthesis Example 1-2]

[1040] Bis-4-aminophenyl sulfide (3.12 g, 14.4 mmol) was changed to m-phenylenediamine (1.56 g, 14.4 mmol), and otherwise, the same operation as in Synthesis Example 1-1 was carried out to obtain 5.4 g of polymer 1A-8.

[1041] The weight-average molecular weight (Mw, polystyrene conversion) of the obtained polymer 1A-8 measured by GPC was 3,500. The units constituting polymer 1A-8 are shown below.

[1042] [Chemical formula 66]

[1043]

[1044] [Examples 1-7 to 1-15 and Comparative Examples 1-1 to 1-5]

[1045] 2.0 parts by mass of a polymer (1A) of the type described in Table 1, a crosslinkable compound (B) of the type and amount described in Table 1, and 0.001 part by mass of a surfactant (D) (BYK-310, manufactured by BYK Chemie) were dissolved in the amount of an organic solvent (S) (cyclopentanone) described in Table 1 to obtain a non-photosensitive liquid composition for each example and each comparative example.

[1046] It should be noted that in Examples 1-14, 1-15, Comparative Example 1-4, and Comparative Example 1-5, the crosslinkable compound was not used.

[1047] The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymers used in the examples and comparative examples are shown in Table 1.

[1048] In Examples 1-7 to 1-13 and Comparative Examples 1-1 to 1-3, the following B-1 to B-3 were used as crosslinkable compounds.

[1049] [Chemical formula 67]

[1050]

[1051] Using the obtained non-photosensitive liquid compositions of Examples 1-7 to 1-15 and Comparative Examples 1-1 to 1-5, the light resistance was evaluated according to the following method.

[1052] <Light resistance evaluation method>

[1053] Using a spin coater, the non-photosensitive liquid composition was coated on a glass substrate. After heating the formed coating film at 100 °C for 1 minute, it was heated at 200 °C for 10 minutes to obtain a cured film.

[1054] For the obtained cured film, a 5 MLx * hr light irradiation was performed using a light resistance testing machine (XT-1500L manufactured by Suga Test Instruments Co., Ltd).

[1055] The light transmittance T1 (%) at a light wavelength of 400 nm of the cured film before light irradiation and the light transmittance T2 (%) at a light wavelength of 400 nm of the cured film after light irradiation were measured respectively. The decrease ΔT (%) in light transmittance caused by light irradiation was calculated using the following formula.

[1056] ΔT (%) = T1 (%) - T2 (%)

[1057] The light resistance of the cured film was evaluated according to the following criteria. A and B are good evaluation results.

[1058] A: ΔT is less than 5%.

[1059] B: ΔT is 5% or more and less than 18%.

[1060] C: ΔT is 18% or more.

[1061] <Refractive index measurement>

[1062] Using an ellipsometer (M-2000UI manufactured by J.A. Woollam Japan Corporation), the refractive index of the cured film formed by the above method at a light wavelength of 550 nm was measured.

[1063] As a result, the refractive indices of the cured films formed from the non-photosensitive liquid compositions of Examples 1-7 to 1-15, Comparative Examples 1-4, and Comparative Example 1-5 were all 1.75 or more.

[1064] On the other hand, the refractive indices of the cured films formed from the non-photosensitive liquid compositions of Comparative Examples 1-1 to 1-3 were all less than 1.75.

[1065]

Table 1

[1066]

[1067] From Examples 1-7 to 1-15, it was found that the non-photosensitive liquid composition containing the polymer (1A) having the unit (A1) represented by formula (A1) and the unit (A2) represented by formula (A2) can provide a cured film having a high refractive index and excellent light resistance.

[1068] On the other hand, from Comparative Examples 1-1 to 1-5, it was found that the non-photosensitive liquid composition containing only the polymer having the unit (A1) represented by formula (A1) cannot provide a cured film having a high refractive index and excellent light resistance.

[1069] Hereinafter, Examples and Comparative Examples related to the second embodiment will be described.

[1070] [Example 2-1]

[1071] Cyanuric chloride (3.69 g, 20 mmol) dissolved in 30 mL of THF was added to a 200 mL three-necked flask, and the liquid in the flask was cooled to 0 °C using an ice bath. Then, while stirring the liquid in the flask, 3-tert-butoxycarbonylaminophenylamine (4.17 g, 20 mmol) dissolved in 90 mL of THF was added dropwise to the flask.

[1072] After the dropwise addition, the reaction solution in the flask was further stirred for 2 hours. An aqueous potassium carbonate solution (prepared by dissolving potassium carbonate (1.66 g, 12 mmol) in 30 mL of pure water) was added to the reaction solution, and the mixture was stirred at room temperature for 20 minutes. After the reaction mixture and 150 mL of ethyl acetate were placed in a separatory funnel, the aqueous phase was removed by liquid separation. THF and ethyl acetate were removed from the recovered organic phase to obtain a solid residue.

[1073] The obtained residue was purified by silica gel chromatography to obtain a dichlorotriazine compound having the following structure, namely 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine.

[1074] [Chemical formula 68]

[1075]

[1076] Charge 3,3'-diaminobenzene (3.90 g, 36.1 mmol) into a 500 mL three-necked flask. Add 150 mL of N,N-dimethylacetamide (DMAc) to the three-necked flask to dissolve 3,3'-diaminobenzene in DMAc. After heating the solution in the three-necked flask to 70 °C, add 2,4-dichloro-6-(3-(tert-butoxycarbonylamino)phenyl)amino-1,3,5-triazine (5.15 g, 14.4 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (5.76 g, 21.7 mmol), which have been dissolved in 150 mL of DMAc, into the three-necked flask to initiate the polymerization reaction.

[1077] After continuing the polymerization at 70 °C for 24 hours, cool the reaction solution to room temperature. Add 2-aminoethanol (2.2 mL, 36.1 mmol) to the cooled reaction solution and stir the reaction solution at room temperature for 1 hour.

[1078] Then, mix the liquid obtained by mixing 10 mL of 28% by mass aqueous ammonia solution, 750 mL of water and 250 mL of methanol with the reaction solution to precipitate the resulting polymer A-1. After recovering the precipitate by filtration, wash the precipitate with 1000 mL of water and 20 mL of hexane. Then, dry the washed precipitate at 100 °C for 24 hours using a vacuum dryer to obtain 11.4 g of polymer 2A-1. The weight-average molecular weight (Mw, polystyrene equivalent) of the obtained polymer 2A-1 measured by GPC is 5,700. The following shows two types of units constituting polymer A-1. Polymer 2A-1 has 2-hydroxyethylamino as the terminal group represented by formula (A1-1).

[1079] [Chemical formula 69]

[1080]

[1081] [Example 2-2]

[1082] Change the amount of 3,3'-diaminobenzene from 3.90 g (36.1 mmol) to 3.00 g (27.8 mmol), and perform the same operations as in Example 2-1 to obtain 9.1 g of polymer 2A-2.

[1083] The weight-average molecular weight (Mw, polystyrene equivalent) of the obtained polymer 2A-2 measured by GPC is 4,500.

[1084] [Example 2-3]

[1085] The amount of m-phenylenediamine was changed from 3.90 g (36.1 mmol) to 2.60 g (24.1 mmol), and otherwise, the operation was the same as in Example 2-1 to obtain 7.8 g of Polymer 2A-3.

[1086] The weight-average molecular weight (Mw, polystyrene conversion) of the obtained Polymer 2A-3 measured by GPC was 4,000.

[1087] [Synthesis Example 2-1]

[1088] 2-Aminoethanol 36.1 mmol was changed to propylamine 36.1 mmol, and otherwise, the operation was the same as in Example 2-1 to obtain 11.2 g of Polymer 2A-4.

[1089] The weight-average molecular weight (Mw, polystyrene conversion) of the obtained Polymer 2A-4 measured by GPC was 5,700. Polymer A-4 has a propylamino group as a terminal group.

[1090] [Synthesis Example 2-2]

[1091] 2-Aminoethanol 36.1 mmol was changed to aniline 36.1 mmol, and otherwise, the operation was the same as in Example 2-1 to obtain 11.5 g of Polymer 2A-5.

[1092] The weight-average molecular weight (Mw, polystyrene conversion) of the obtained Polymer 2A-5 measured by GPC was 5,700. Polymer 2A-5 has a phenylamino group as a terminal group.

[1093] [Examples 2-4 to 2-6, Comparative Example 2-1 and Comparative Example 2-2]

[1094] 2.0 parts by mass of a polymer (2A) of the type described in Table 2, 0.4 part by mass of a crosslinkable compound (B) having the following structure, and 0.001 part by mass of a surfactant (D) (BYK-310, manufactured by BYK Chemie) were dissolved in 6.5 parts by mass of an organic solvent (S) (cyclopentanone) to obtain a non-photosensitive liquid composition for each example and each comparative example.

[1095] [Chemical Formula 70]

[1096]

[1097] The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer (2A) used in the examples and comparative examples are shown in Table 2.

[1098] Using the obtained non-photosensitive liquid compositions of Examples 2-4 to 2-6, Comparative Example 2-1 and Comparative Example 2-2, the heat resistance was evaluated by the following method.

[1099] <Method for evaluating heat resistance>

[1100] Using a spin coater, a non-photosensitive liquid composition was coated on a glass substrate. After heating the formed coating film at 100 °C for 1 minute, it was heated at 200 °C for 10 minutes to obtain a cured film.

[1101] In an oven, the obtained cured film was heated at 220 °C for 5 hours.

[1102] The light transmittance T1 (%) at a light wavelength of 400 nm of the cured film before heating and the light transmittance T2 (%) at a light wavelength of 400 nm of the cured film after heating were measured respectively. The reduction ΔT (%) in light transmittance due to heating was calculated using the following formula.

[1103] ΔT (%) = T1 (%) - T2 (%)

[1104] The heat resistance of the cured film was evaluated according to the following criteria. A represents a good evaluation result.

[1105] A: ΔT is less than 5%.

[1106] B: ΔT is 5% or more.

[1107] <Refractive index measurement>

[1108] Using an ellipsometer (M-2000UI manufactured by J.A. Woollam Japan Corporation), the refractive index at a light wavelength of 550 nm of the cured film formed by the above method was measured.

[1109] As a result, the refractive indices of the cured films formed using the non-photosensitive liquid compositions of Examples 2-4 to 2-6, Comparative Example 2-1, and Comparative Example 2-2 were all 1.75 or more.

[1110]

Table 2

[1111]

[1112] From Examples 2-4 to 2-6, it can be seen that a non-photosensitive liquid composition containing a polymer (2A) having a unit (A1) represented by formula (A1) and a terminal group represented by formula (A1-1) can provide a cured film with a high refractive index and excellent heat resistance.

[1113] On the other hand, from Comparative Example 2-1 and Comparative Example 2-2, it can be seen that a non-photosensitive liquid composition containing a polymer containing a unit (A1) represented by formula (A1) but not having a terminal group represented by formula (A1-1) cannot provide a cured film with excellent heat resistance.

[1114] Examples and comparative examples related to the third embodiment are described below.

[1115] [Example 3-1]

[1116] Cyanuric chloride (3.69 g, 20 mmol) dissolved in 30 mL of THF was added to a 200 mL three-necked flask, and the liquid in the flask was cooled to 0 °C using an ice bath. Then, while stirring the liquid in the flask, 3-tert-butoxycarbonylaminophenylamine (4.17 g, 20 mmol) dissolved in 90 mL of THF was added dropwise to the flask.

[1117] After the addition, stirring of the reaction solution in the flask was continued for 2 hours. An aqueous potassium carbonate solution (prepared by dissolving potassium carbonate (1.66 g, 12 mmol) in 30 mL of pure water) was added to the reaction solution, and the mixture was stirred at room temperature for 20 minutes. After the reaction mixture and 150 mL of ethyl acetate were placed in a separatory funnel, the aqueous phase was removed by liquid separation. THF and ethyl acetate were removed from the recovered organic phase to obtain a solid residue.

[1118] The obtained residue was purified by silica gel chromatography to obtain a dihalotriazine compound having the following structure, 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine.

[1119] [Chemical formula 71]

[1120]

[1121] m-Phenylenediamine (1.56 g, 14.4 mmol) was placed in a 200 mL three-necked flask. 60 mL of N,N-dimethylacetamide (DMAc) was added to the three-necked flask to dissolve m-phenylenediamine in DMAc. After heating the solution in the three-necked flask to 70 °C, 2,4-dichloro-6-(3-tert-butoxycarbonylaminophenyl)amino-1,3,5-triazine (2.06 g, 5.76 mmol) and 2,4-dichloro-6-(4-cyanophenyl)amino-1,3,5-triazine (2.30 g, 8.64 mmol) dissolved in 60 mL of DMAc were added to the three-necked flask to initiate a polymerization reaction.

[1122] After continuing the polymerization at 70 °C for 24 hours, the reaction solution was cooled to room temperature. Propylamine (5.92 mL, 72.0 mmol) was added to the cooled reaction solution, and the reaction solution was stirred at room temperature for 1 hour.

[1123] Then, a liquid prepared by mixing 4 mL of an aqueous ammonia solution with a concentration of 28% by mass, 300 mL of water, and 100 mL of methanol was mixed with the reaction solution to precipitate the resulting polymer 3A-1. After recovering the precipitate by filtration, the precipitate was washed with 400 mL of water and 20 mL of hexane. Then, the washed precipitate was dried at 100 °C for 24 hours using a vacuum dryer to obtain 4.62 g of polymer 3A-1. The weight-average molecular weight (Mw, in terms of polystyrene conversion) of the obtained polymer 3A-1 measured by GPC was 6,000. The following shows two types of units constituting polymer 3A-1.

[1124] [Chemical formula 72]

[1125]

[1126] [Example 3-2]

[1127] The polymerization reaction temperature was changed from 70 °C to 60 °C, and otherwise, the operation was the same as in Example 3-1 to obtain 4.59 g of polymer 3A-2.

[1128] The weight-average molecular weight (Mw, in terms of polystyrene conversion) of the obtained polymer 3A-2 measured by GPC was 5,000.

[1129] [Synthesis Example 3-1]

[1130] The polymerization reaction temperature was changed from 70 °C to 60 °C, and the polymerization reaction time was changed from 24 hours to 6 hours. Otherwise, the operation was the same as in Example 3-1 to obtain 4.54 g of polymer 3A-3.

[1131] The weight-average molecular weight (Mw, in terms of polystyrene conversion) of the obtained polymer 3A-3 measured by GPC was 3,000.

[1132] [Example 3-3, Example 3-4, and Comparative Example 3-1]

[1133] 2.0 parts by mass of a polymer (3A) of the type described in Table 3, 0.4 part by mass of a crosslinkable compound (B) having the following structure, and 0.001 part by mass of a surfactant (D) (BYK-310, manufactured by BYK Chemie) were dissolved in 6.5 parts by mass of an organic solvent (S) (cyclopentanone) to obtain the non-photosensitive liquid compositions of Example 3-3, Example 3-4, and Comparative Example 3-1.

[1134] [Chemical formula 73]

[1135]

[1136] The weight-average molecular weight (Mw) and dispersity (Mw / Mn) of the polymer (3A) used in Example 3-3, Example 3-4, and Comparative Example 3-1 are shown in Table 3.

[1137] Using the obtained non-photosensitive liquid compositions of Example 3-3, Example 3-4, and Comparative Example 3-1, the light resistance and heat resistance were evaluated according to the following methods.

[1138] <Light Resistance Evaluation Method>

[1139] Using a spin coater, the non-photosensitive liquid composition was coated on a glass substrate. After heating the formed coating film at 100 °C for 1 minute, it was heated at 200 °C for 10 minutes to obtain a cured film.

[1140] For the obtained cured film, a 5 MLx * hr light irradiation was performed using a light resistance testing machine (XT-1500L manufactured by Suga Test Instruments Co., Ltd).

[1141] The light transmittance T1 (%) at a light wavelength of 400 nm of the cured film before light irradiation and the light transmittance T2 (%) at a light wavelength of 400 nm of the cured film after light irradiation were measured respectively. The decrease ΔT (%) in light transmittance caused by light irradiation was calculated using the following formula.

[1142] ΔT (%) = T1 (%) - T2 (%)

[1143] The light resistance of the cured film was evaluated according to the following criteria. A and B are good evaluation results.

[1144] A: ΔT is less than 5%.

[1145] B: ΔT is 5% or more and less than 18%.

[1146] C: ΔT is 18% or more.

[1147] <Heat Resistance Evaluation Method>

[1148] Using a spin coater, the non-photosensitive liquid composition was coated on a glass substrate. After heating the formed coating film at 100 °C for 1 minute, it was heated at 200 °C for 10 minutes to obtain a cured film.

[1149] In an oven, the obtained cured film was heated at 150 °C for 500 hours.

[1150] Measure the light transmittance Ta (%) at a light wavelength of 400 nm of the cured film before heating and the light transmittance Tb (%) at a light wavelength of 400 nm of the cured film after heating, respectively. Calculate the reduction ΔT (%) in light transmittance caused by heating using the following formula.

[1151] ΔT (%) = Ta (%) - Tb (%)

[1152] Evaluate the heat resistance of the cured film according to the following criteria. A represents a good evaluation result.

[1153] A: ΔT is less than 5%.

[1154] B: ΔT is 5% or more.

[1155] <Refractive index measurement>

[1156] Using an ellipsometer (M-2000UI manufactured by J.A. Woollam Japan Corporation), measure the refractive index at a light wavelength of 550 nm of the cured film formed by the above method.

[1157] As a result, the refractive indices of the cured films formed using the non-photosensitive liquid compositions of Example 3-3, Example 3-4, and Comparative Example 3-1 are all 1.75 or more.

[1158]

Table 3

[1159]

[1160] From Example 3-3 and Example 3-4, it can be seen that a non-photosensitive liquid composition containing a polymer (3A) containing a unit (A1) represented by formula (A1) and having a weight average molecular weight of 4,000 or more and 20,000 or less can provide a cured film with a high refractive index, excellent light resistance, and excellent heat resistance.

[1161] On the other hand, from Comparative Example 3-1, it can be seen that a non-photosensitive liquid composition containing a polymer containing a unit (A1) represented by formula (A1) and having a weight average molecular weight of less than 4,000 can provide a cured film with a high refractive index, but provides a cured film with poor light resistance and heat resistance.

Claims

1. A polymer containing a triazine ring, which comprises a structural unit represented by the following formula (A1) and a structural unit represented by the following formula (A2), [Chemical formula 1] In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group. The hydroxyl group protected with the acetal protecting group is -O-CHR A1 -O-R A2 represented by the group R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The said R A1 and the said R A2 can be bonded to each other to form a ring, X 1 and X 2 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group which is Ar 1 as described X 2 bonded to the aromatic ring in the group containing an aromatic group which is Ar 2 ; [Chemical formula 2] In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group, X 1 and X 2 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group which is Ar 3 , X 2 bonded to the aromatic ring in the group containing an aromatic group which is Ar 2 .

2. The polymer containing a triazine ring as described in claim 1, wherein, The ratio of the number of moles of the structural unit represented by the formula (A1) to the total number of moles of the structural unit represented by the formula (A1) and the structural unit represented by the formula (A2) is 10 mol% or more and 70 mol% or less.

3. The polymer containing a triazine ring as claimed in claim 1, wherein, R a1 is tert-butoxycarbonylamino or tert-butoxycarbonyloxy.

4. The polymer containing a triazine ring as described in claim 1, wherein, X in the formula (A1) and the formula (A2) 2 is -NR a2 - or -O-.

5. A polymer containing a triazine ring, which comprises a structural unit represented by the following formula (A1), At least a part of the terminal of the molecular chain of the polymer containing a triazine ring has a group represented by the following formula (A1-1), [Chemical formula 3] In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group, The hydroxyl group protected with the acetal protecting group is -O-CHR A1 -O-R A2 represented by the group R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The R A1 and the R A2 can be bonded to each other to form a ring, X 1 and X 2 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group which is Ar 1 ​ X 2 bonded to the aromatic ring in the group containing an aromatic group as Ar 2 ; -X 2 -X 3 -X 4 ···(A1-1) In formula (A1-1), X 2 is the same as X in formula (A1) 2 Similarly, X 3 is a divalent hydrocarbon group, X 4 is -OR a3 or -N(R a3 )2, R a3 is a hydrogen atom or an alkyl group which may have substituents, When the hydrocarbon group as X 3 is a group containing an aromatic group, X 4 is not an amino group.

6. The polymer containing a triazine ring according to claim 5, wherein, R a1 is a tert-butoxycarbonylamino group or a tert-butoxycarbonyloxy group.

7. The polymer containing a triazine ring as described in claim 5, wherein, The said X 2 is -NR a2 - or -O-.

8. The polymer containing a triazine ring as claimed in claim 5, wherein, As the X 3 The divalent hydrocarbon group is an alkylene group.

9. The polymer containing a triazine ring according to claim 5, which comprises a structural unit represented by the following formula (A2), [Chemical formula 4] In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group, X 1 and X 2 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 3 , X 2 bonded to the aromatic ring in the group containing an aromatic group which is Ar 2 .

10. A polymer containing a triazine ring, which comprises a structural unit represented by the following formula (A1), The weight-average molecular weight of the polymer containing a triazine ring is 4,000 or more and 20,000 or less, [Chemical formula 5] In formula (A1), Ar 1 and Ar 2 are groups containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group, The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -O-R A2 represented by the group R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The said R A1 and the said R A2 can be bonded to each other to form a ring, X 1 and X 2 each independently is -NR a2 -, -O-, or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 1 thereof, X 2 bonded to the aromatic ring in the group containing an aromatic group which is Ar 2 .

11. The polymer containing a triazine ring as claimed in claim 10, wherein, R a1 is a tert-butoxycarbonylamino group or a tert-butoxycarbonyloxy group.

12. The polymer containing a triazine ring according to claim 10, wherein, Said X 2 is -NR a2 - or -O-.

13. The polymer containing a triazine ring according to claim 10, which comprises a structural unit represented by the following formula (A2), [Chemical formula 6] In formula (A2), Ar 2 and Ar 3 are groups containing an aromatic group, X 1 and X 2 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group which is Ar 3 ​ X 2 bonded to the aromatic ring in the group containing an aromatic group which is Ar 2 .

14. A method for producing the polymer containing a triazine ring according to claim 1, which comprises a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3), The dihalotriazine compound comprises a compound represented by the following formula (A3) and a compound represented by the following formula (A6), Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3) In formulas (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent; [Chemical formula 7] In formula (A3), Hal is a halogen atom, Ar 1 is a group containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group, The hydroxyl group protected with the acetal protecting group is -O-CHR A1 -O-R A2 a group represented by R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The R A1 and the R A2 can be bonded to each other to form a ring, X 1 each independently being -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 1 ; [Chemical formula 7] In formula (A6), Hal is a halogen atom, Ar 3 is a group containing an aromatic group, X 1 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 3 ​ 15. A method for producing the polymer containing a triazine ring according to claim 5, which comprises a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3), The dihalotriazine compound comprises a compound represented by the following formula (A3), The condensation of the dihalotriazine compound with the compound represented by any one of the formulas (A5-1) to (A5-3) is carried out in the presence of a compound represented by any one of the following formulas (A7-1) to (A7-3), or The condensation product of the dihalotriazine compound with the compound represented by any one of the formulas (A5-1) to (A5-3) is reacted with the compound represented by any one of the formulas (A7-1) to (A7-3), Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3) In Formulae (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent; [Chemical formula 8] In formula (A3), Hal is a halogen atom, Ar 1 is a group containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group, The hydroxyl group protected with the acetal protecting group is a group represented by -O-CHR A1 -O-R A2 as described above R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The R A1 and the R A2 can be bonded to each other to form a ring, X 1 each independently being -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 1 ; X 4 -X 3 -NR a2 H···(A7-1) X 4 -X 3 -OH···(A7-2) X 4 -X 3 -SH···(A7-3) In formulas (A7-1) to (A7-3), X 3 and X 4 are the same as X 3 and X 4 in formula (A1-1). R a2 Same as R in formula (1) a2 Similarly.

16. The manufacturing method according to claim 15, wherein, The dihalotriazine compound comprises a compound represented by the following formula (A6), [Chemical formula 9] In formula (A6), Hal is a halogen atom, Ar 3 is a group containing an aromatic group, X 1 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group which is Ar 3 .

17. A method for producing the polymer containing a triazine ring according to claim 10, which comprises a step of condensing a dihalotriazine compound with a compound represented by any one of the following formulas (A5-1) to (A5-3), The dihalotriazine compound comprises a compound represented by the following formula (A3), Ar 2 -(NR a2 H)2···(A5-1) Ar 2 -(OH)2···(A5-2) Ar 2 -(SH)2···(A5-3) In Formulae (A5-1) to (A5-3), Ar 2 is a group containing an aromatic group, and R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent; [Chemical formula 10] In formula (A3), Hal is a halogen atom, Ar 1 is a group containing an aromatic group, R a1 is tert-butoxycarbonyloxy, tert-butoxycarbonylamino, or a hydroxyl group protected with an acetal protecting group, or is a carboxyl group protected with an acid dissociable group The hydroxyl group protected by the acetal protecting group is -O-CHR A1 -O-R A2 represented by the group R A1 is a hydrogen atom or an alkyl group, R A2 is an alkyl group, The said R A1 and the said R A2 can be bonded to each other to form a ring, X 1 each independently being -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 1 ​ 18. The manufacturing method according to claim 17, wherein, The condensation of the dihalotriazine compound and the compound represented by any one of the formulas (A5-1) to (A5-3) is carried out under the conditions of 40 °C or higher and 100 °C or lower, and 120 minutes or longer and 48 hours or shorter.

19. The manufacturing method according to claim 17, wherein, When the condensation of the dihalotriazine compound and the compound represented by any one of the formulas (A5-1) to (A5-3) is carried out, the total concentration of the dihalotriazine compound and the compound represented by any one of the formulas (A5-1) to (A5-3) in the reaction solution is 120 mmol / L or higher.

20. The manufacturing method according to claim 17, wherein, The dihalotriazine compound includes a compound represented by the following formula (A6), [Chemical formula 11] In the formula (A6), Hal is a halogen atom, Ar 3 is a group containing an aromatic group, X 1 each independently is -NR a2 -, -O- or -S-, R a2 is a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent, X 1 bonded to the aromatic ring in the group containing an aromatic group as Ar 3 ​ 21. A non-photosensitive liquid composition, comprising: an organic solvent (S); and a polymer (1A) containing a triazine ring, a polymer (2A) containing a triazine ring, or a polymer (3A) containing a triazine ring, The polymer (1A) containing a triazine ring is the polymer containing a triazine ring according to claim 1, The polymer (2A) containing a triazine ring is the polymer containing a triazine ring according to claim 5, The polymer (3A) containing a triazine ring is the polymer containing a triazine ring according to claim 10, In the case where R a1 is a hydroxyl group protected with an acetal protecting group or a carboxyl group protected with an acid dissociable group, the non-photosensitive liquid composition further contains a thermal acid generator (C).

22. The non-photosensitive liquid composition according to claim 21, further comprising a crosslinkable compound (B).

23. The non-photosensitive liquid composition according to claim 22, wherein, The crosslinkable compound (B) is an aromatic compound (Bi) containing two or more crosslinkable groups, a triazine ring, a fluorene ring which may have a substituent or a binaphthalene ring which may have a substituent, or a sulfur-containing compound (Bii) containing two or more crosslinkable groups, or an isocyanate compound (Biii) containing two or more isocyanate groups, or an aliphatic compound (Biv) containing two or more crosslinkable groups, The sulfur-containing compound (Bii) is a compound that does not belong to the aromatic compound (Bi), The isocyanate compound (Biii) is a compound that does not belong to the aromatic compound (Bi) and the sulfur-containing compound (Bii), The aliphatic compound (Biv) is a compound that does not belong to the sulfur-containing compound (Bii) and the isocyanate compound (Biii).

24. The non-photosensitive liquid composition according to claim 23, wherein, The crosslinkable group is an epoxy group, a thiirane group or an isocyanate group.

25. The non-photosensitive liquid composition according to claim 21, wherein, The organic solvent (S) is a ketone, a nitrogen-containing polar organic solvent, a monoalkyl ether acetate of a diol, or a monoalkyl ether of a diol.

26. A method for manufacturing a molded article, comprising the following steps: a step of molding the non-photosensitive liquid composition according to claim 21; and a step of removing the organic solvent (S) from the molded non-photosensitive liquid composition by heating.

27. The manufacturing method of the molded body according to claim 26, wherein, The non-photosensitive liquid composition is molded into a film shape by coating the non-photosensitive liquid composition on a substrate.

28. A molded article of the non-photosensitive liquid composition according to claim 21.

29. An optical component formed from the molded article according to claim 28.

30. The optical component according to claim 29, which is a film or a microlens.

31. An optical element comprising the optical component according to claim 29.

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